Fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, herbicide and method for using the same

ABSTRACT

A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I):  
                 
 
     wherein R 1  is H, (C 1 -C 6 ) alkyl; R 2  and R 3  are H, (halo) (C 1 -C 6 ) alkyl, (C 3 -C 1 ) cycloalkyl, substituted amino (C 1 -C 6 ) alkyl, (substituted) phenyl (C 1 -C 1 ) alkyl, (substituted) phenyl (C 1 -C 6 ) alkoxy or the like or R 2  and R 3 , taken conjointly, represent a (substituted) 5- or 6-membered heterocycle having at least one of O, S and N; X is H, halogen, NO 2 , CN, (C 1 -C 6 ) alkyl, (substituted) phenyl, (substituted) phenoxy or the like;  
                 
 
     is  
                 
 
     or the like wherein Y, R 4  and R 9  are H, halogen, NO 2 , CN, (C 1 -C 6 ) alkyl or the like, and A, B, D, E, F, G, J and K are O, S, N, sulfinyl or the like; and a herbicide containing said derivative as active ingredient.

TECHNICAL FIELD

[0001] The present invention relates to novel fused heterocyclic dicarboxylic acid diamide derivatives or salts thereof, a herbicide containing said compound or salt thereof as an active ingredient, and a method for using said herbicide.

BACKGROUND ART

[0002] In JP-A-6-2519, there is mentioned that pyrazinedicarboxylic acid diamide derivatives are useful as herbicide. In JP-A-9-323974, there is mentioned that pyridinedicarboxylic acid diamide derivatives are useful as herbicide.

DISCLOSURE OF THE INVENTION

[0003] The present inventors have conducted extensive studies with the aim of developing a novel herbicide. As a result, it has been found that the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) of the present invention or salts thereof are novel compounds not found in literature and having an excellent herbicidal activity. Based on this finding, the present invention has been accomplished.

[0004] The present invention relates to fused heterocyclic dicarboxylic acid diamide derivatives represented by the following general formula (I):

[0005] wherein R¹ represents hydrogen atom or (C₁-C₆) alkyl group;

[0006] R² and R³ may be same or different and each represents hydrogen atom, (C₁-C₈) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₈) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, alkylthio (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, amino (C₁-C₆) alkyl group, substituted amino (C₁-C₆) alkyl group substituted with one or two, same or different (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₆) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkoxy group or substituted phenyl (C₁-C₆) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups; or

[0007] R² and R³, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group and halo (C₁-C₆) alkylthio group;

[0008] X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₁) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C₁-C₆) alkyl groups, cyano (C₁-C₆) alkyl groups, phenyl (C,-C₁) alkyl groups, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl groups, (C₁-C₆) acyl groups, (C₁-C₆) alkylsulfonyl groups or halo (C₁-C₆) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₁) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₁) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₁) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenyl (C₁-C₆) alkyl group or substituted phenyl (C₁-C₆) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group; and

[0009] represents Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, Q⁷, Q⁸, Q⁹, Q¹⁰, Q¹¹, Q¹², Q¹³ or Q¹⁴, wherein:

[0010] Q¹ is a group of the following formula:

[0011] wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₁) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆)) alkyl group, (C₁-C₆) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₆) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group, (C₃-C₅) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C₁-C₆) alkyl groups; and

[0012] R⁴ represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (c₃-c₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₁) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, methylenedioxy group, amino group and substituted amino group substituted with at least one, same or different (C₁-C₆) alkyl groups, cyano (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl groups, (C₁-C₆) alkoxyaminocarbonyl groups, (C₁-C₆) acyl groups, (C₁-C₆) alkylsulfonyl groups, halo (C₁-C₆) alkylsulfonyl groups or phenyl (C₁-C₆) alkyl groups;

[0013] Q² is a group of the following formula:

[0014] wherein at least one of A, B, D and E represent a nitrogen atom, and the others of A, B, D and E represent C-R⁵ wherein R⁵ represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₁) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, amino group or substituted amino group having at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₆) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group; and Y is as defined above;

[0015] Q³ is a group of the following formula:

[0016] wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R⁶ wherein R⁶ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group or halo (C₁-C₆) alkylsulfonyl group, and the others of F, G, J and K each represents C—(R⁷)R⁸ wherein R⁷ and R⁸ may be same or different and represent hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₆) alkyl group substituted with at least one, same or different halogen atoms or (C₁-C₆) alkyl groups, amino (C₁-C₆) alkyl group, substituted amino (C₁-C₆) alkyl group substituted with at least one, same or different (C₁-C₆) alkyl groups or phenyl (C₁-C₆) alkoxy group; and Y is as defined above; and G and J may be taken conjointly to represent CH═CH;

[0017] Q⁴ is a group of the following formula:

[0018] wherein R⁹ is same or different and represents halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, amino group, substituted amino group substituted with at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₁) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group, (C₃-C₅) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C₁-C₆) alkyl groups; m represents an integer of 0 to 2;

[0019] Z represents oxygen atom, sulfur atom or N-R¹⁰ wherein R¹⁰ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group or (C₁-C₆) alkylthio (C₁-C₆) alkyl group; and Y is as defined above;

[0020] Q⁵ is a group of the following formula:

[0021] wherein R⁹, Y, Z and m are as defined above;

[0022] Q⁶ is a group of the following formula:

[0023] wherein R⁹, Y, Z and m are as defined above;

[0024] Q⁷ is a group of the following formula:

[0025] wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R¹¹ wherein R¹¹ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) cycloalkyl group, (C₁-C₁) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group or (C₁-C₆) alkylthio (C₁-C₆) alkyl group, and the others of L, M and T each represents C—(R¹²)R¹³ wherein R¹² and R¹³ may be same or different and each represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₆) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkoxy group, substituted phenyl (C₁-C₆) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, amino (C₁-C₆) alkyl group or substituted amino (C₁-C₆) alkyl group substituted with at least one, same or different (C₁-C₆) alkyl groups;

[0026] Q⁸ is a group of the following formula:

[0027] wherein R¹⁴ represents hydrogen atom or is the same as R⁹, and Y and Z are as defined above;

[0028] Q⁹ is a group of the following formula:

[0029] wherein R¹⁴, Y and Z are as defined above;

[0030] Q¹⁰ is a group of the following formula:

[0031] wherein R¹⁴, Y and Z are as defined above;

[0032] Q¹ is a group of the following formula:

[0033] wherein R¹⁴ Y and Z are as defined above;

[0034] Q¹² is a group of the following formula:

[0035] wherein R¹⁴, Y and Z are as defined above;

[0036] Q¹³ is a group of the following formula:

[0037] wherein R¹⁴, Y and Z are as defined above; and

[0038] Q¹⁴ is a group of the following formula:

[0039] wherein R⁹ is as defined above and n represents an integer of 0 to 4; and

[0040] salts of said compounds, a herbicide containing said compound as an active ingredient, and a method for using said herbicide.

[0041] In the definitions of the substituents in the fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) or salts thereof, the term “halogen atom” means chlorine atom, bromine atom, iodine atom or fluorine atom; the term (C₁-C₈) means that the number of carbon atoms is 1 to 8; the term (C₁-C₈) alkyl group, for example, means a straight chain or branched chain alkyl group having 1 to 8 carbon atoms; and the term “halo (C₁-C₆) alkyl group” means a straight chain or branched chain alkyl group having 1 to 6 carbon atoms and substituted with at least one, same or different halogen atoms.

[0042] As examples of the salt, inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salts of metal ions such as sodium ion, potassium ion, calcium ion and the like can be referred to.

[0043] As a preferable embodiment of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I), a case where R¹ and R² are both hydrogen atom, R³ is (C₁-C₈) alkyl group or (C₃-C₈) cycloalkyl group, X is halogen atom or (C₁-C₆) alkyl group, and

[0044] is Q², Q³, Q⁴, Q⁶, Q⁷, Q⁸, Q¹¹ or the like can be referred to. As a further preferable embodiment, cases where X is substituted at the 2- and 3-positions or at the 2-, 3- and 6-positions can be referred to.

[0045] The fused heterocyclic dicarboxylic acid diamide derivatives represented by general formula (I) can be produced, for example, according to the production process schematically shown below.

[0046] Production Process

[0047] wherein R², R³, X and

[0048] are as defined above, and hal represents a halogen atom.

[0049] A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I-1) can be produced by hydrolyzing a compound represented by general formula (VIII) in the presence of an acid or an alkali to form a dicarboxylic acid represented by general formula (VII), converting it into an acid anhydride (VI) in the presence of a dehydrating agent, reacting the acid anhydride with a substituted aniline (V) in the presence or absence of an inert solvent to form anilides (IV-1) and (IV-2), and then after isolating or without isolating them, reacting them with a dehydrating agent in the presence or absence of an inert solvent to form imides represented by general formula (III), and after isolating or without isolating the imides (III), reacting them with an amine or a salt thereof represented by general formula (II-1) or (II-2) in the presence or absence of an inert solvent.

[0050] A. General formula (VIII)→General formula (VII)

[0051] As the inert solvents which can be used in this reaction, for example, water, water-soluble solvents such as methanol, ethanol, propanol and the like and mixtures of the water-soluble solvents can be referred to.

[0052] As the base which can be used for the hydrolysis, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like can be referred to. The amount of the base may be appropriately selected from a range of 2 to 10 equivalents per equivalent of the diester of general formula (VIII).

[0053] The reaction can be carried out at a temperature ranging from ambient temperature to the reflux temperature of the used inert solvent. The reaction time may vary with scale and temperature of the reaction, and it may be appropriately selected from a range of several minutes to 48 hours.

[0054] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0055] It is also possible to use the product obtained in this step in the subsequent reaction without isolation.

[0056] B. General formula (VII)→General formula (VI)

[0057] The inert solvent used in this reaction may be any inert solvent so far as its use does not obstruct the progress of this reaction greatly. Examples of the inert solvent include halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and the like; acyclic and cyclic ethers such as methyl cellosolve, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and the like; and organic acids such as acetic acid, trifluoroacetic acid and the like. These inert solvents may be used either alone or in the form of a mixture.

[0058] It is also possible to replace the inert solvent with an excessive quantity of the dehydrating agent.

[0059] As the dehydrating agent, for example, acetic anhydride, trifluoroacetic anhydride and the like can be used. The amount of these dehydrating agents may be appropriately selected from a range of from equi-molar quantity to excessive molar quantity per mol of the compound of general formula (VII). Preferably the dehydrating agent is used in an equimolar quantity.

[0060] The reaction temperature may be appropriately selected in a range of from ambient temperature to the boiling point range of the used inert solvent. When no inert solvent is used, the reaction may be carried out in the boiling point range of the used dehydrating agent.

[0061] The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.

[0062] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0063] This reaction can be carried out according to the description of J. Org. Chem. Soc., 52, 129 (1987); J. Am. Chem. Soc., 51, 1865 (1929); ibid., 63, 1542 (1941); etc.

[0064] It is also possible to use the objective product in the subsequent reaction without isolation.

[0065] C. General formula (VI)→General formula (IV-1)+General formula (IV-2)

[0066] As the inert solvent used in this reaction, any inert solvent may be used so far as it does not obstruct progress of the reaction greatly. Examples of the inert solvent include aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene, dichlorobenzene and the like; acyclic and cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and the like; esters such as ethyl acetate and the like; amides such as dimethylformamide, dimethylacetamide and the like; acids such as acetic acid and the like; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; water and the like. These inert solvents may be used either alone or in the form of a mixture of two or more.

[0067] Since this reaction is an equimolar reaction, the reactants may be used in equimolar amounts. It is also possible, however, to use any of the reactants in an excessive amount. If desired, this reaction may be carried out under a dehydrating condition.

[0068] The reaction temperature may be appropriately selected in a range of from ambient temperature to the boiling point range of the used inert solvent. When no inert solvent is used, the reaction may be carried out in the boiling point range of the used dehydrating agent.

[0069] The reaction time may vary with scale and temperature of the reaction, and it ranges from several minutes to 48 hours.

[0070] After completion of the reaction, the objective product is isolated from the reaction mixture containing it according to a conventional method, and then the product is purified by recrystallization, distillation, column chromatography or the like according to the need, whereby the objective product can be obtained.

[0071] It is also possible to use the objective product in the subsequent reaction without isolation.

[0072] D. General formula (IV-1) +General formula (IV-2)→General formula (III)

[0073] This reaction can be carried out in the same manner as B, whereby the objective product can be obtained. It is also possible to use the objective product in the subsequent reaction without isolation.

[0074] Hereunder are shown typical examples of the imide represented by general formula (III).

[0075] (1). N-(3-Chloro-2,6-diethylphenyl)-1,3-dimethylpyrazolo[5,4-b]pyridine-5,6-dicarboximide ¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0076] 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0077] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0078] 2.69(3H,s), 4.26(3H,s), 7.21(1H,d,J=8.4 Hz),

[0079] 7.47(1H,d,J=8.4 Hz), 8.61(1H,s)

[0080] (2). N-(3-chloro-2,6-diethylphenyl)thieno[3,2-b]pyridine-5,6-dicarboximide ¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0081] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz), 2.44 (2H,q,J=7.5 Hz), 2.63(2H,q,J=7.5 Hz),

[0082] 7.20(1H,d,J=8.4 Hz), 7.47(1H,d,J=8.4 Hz),

[0083] 7.90(1H,d,J=5.7 Hz), 8.17(1H,d,J=5.7 Hz),

[0084] 8.79(1H,s).

[0085] (3). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[3,2-b]pyridine-5,6-dicarboximide ¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0086] 1.06(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz),

[0087] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz), 3.51-3.68(4H,m), 7.17(1H,d,J=8.4 Hz),

[0088] 7.44(1H,d,J=8.4 Hz), 7.95(1H,s).

[0089] (4). N-(3-chloro-2,6-diethylphenyl)-2,3-dihydrothieno-[2,3-b]pyridine-5,6-dicarboximide ¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0090] 1.05(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz),

[0091] 2.38(2H,q,J=7.5 Hz), 2.57(2H,q,J=7.5 Hz), 3.47-3.61(4H,m), 7.16(1H,d,J=8.4 Hz),

[0092] 7.43(1H,d,J=8.4 Hz), 7.85(1H,s).

[0093] (5). N-(3-chloro-2,6-diethylphenyl)-furo[2,3-b]pyridine-5,6-dicarboximide ¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0094] 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0095] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0096] 7.11(1H,d,J=2.6 Hz), 7.24(1H,d,J=8.4 Hz),

[0097] 7.47(1H,d,J=8.4 Hz), 8.05(1H,d,J=2.6 Hz),

[0098] 8.53(1H,s).

[0099] (6). N-(3-chloro-2,6-diethylphenyl)-1-methyl-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide

[0100]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0101] 1.04(3H,t,J=7.5 Hz), 1.08(3H,t,J=7.5 Hz),

[0102] 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0103] 3.93(3H,s), 6.95(1H,d,J=0.6 Hz),

[0104] 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz),

[0105] 7.61(1H,d,J=0.6 Hz), 8.17(1H,s).

[0106] (7). N-(3-chloro-2,6-diethylphenyl)-1-methoxy-pyrrolo-[3,2-b]pyridine-5,6-dicarboximide

[0107]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0108] 1.06(3H,t,J=7.5 Hz), 1.11(3H,t,J=7.5 Hz),

[0109] 2.42(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0110] 4.21(3H,s), 6.90(1H,d,J=0.6 Hz),

[0111] 7.15(1H,d,J=8.0 Hz), 7.38(1H,d,J=8.0 Hz),

[0112] 7.81(1H,d,J=0.6 Hz), 8.32(1H,s)

[0113] (8). N-(3-chloro-2,6-diethylphenyl)-1,8-naphthylidine-2,3-dicarboximide

[0114]¹H-NMR [TMS/CDCl₃, δ (ppm)

[0115] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0116] 2.43(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0117] 7.24(1H,d,J=8.4 Hz), 7.52(1H,d,J=8.4 Hz),

[0118] 8.05(1H,dd,J=2.9 and 7.9 Hz), 8.81(1H,d,J=7.9 Hz),

[0119] 9.04(1H,s), 9.62(1H,d,J=2.9 Hz).

[0120] (9). N-(3-chloro-2,6-diethylphenyl)-5-oxo-5,6,7,8-tetrahydroquinoline-2,3-dicarboximide

[0121]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0122] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0123] 2.30(2H,m), 2.43(2H,q,J=7.5 Hz), 2.48(2H,m),

[0124] 2.61(2H,q,J=7.5 Hz), 2.85(2H,m),

[0125] 7.19(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz),

[0126] 8.89(1H,s).

[0127] (10). N-(3-chloro-2,6-diethylphenyl)-6-methyl-5,6,7,8-tetrahydro-1,6-naphthylidine-2,3-dicarboximide

[0128]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0129] 1.09(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0130] 2.33(2H,q,J=7.5 Hz), 2.52(2H,q,J=7.5 Hz),

[0131] 2.95(3H,s), 3.00-3.12(4H,m), 3.54(2H,m),

[0132] 7.15(1H,d,J=8.4 Hz), 7.42(1H,d,J=8.4 Hz),

[0133] 8.02(1H,s).

[0134] (11). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-thiopyrano[4,3-b]pyridine-2,3-dicarboximide

[0135]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0136] 1.08(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0137] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz),

[0138] 3.11(2H,t,J=5.8 Hz), 3.52(2H,t,J=5.8 Hz),

[0139] 3.97(2H,s), 7.19(1H,d,J=8.4 Hz),

[0140] 7.46(1H,d,J=8.4 Hz), 8.08(1H,s).

[0141] (12). N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2,3-dicarboximide

[0142]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0143] 1.07(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0144] 2.39(2H,q,J=7.5 Hz), 2.58(2H,q,J=7.5 Hz),

[0145] 3.31(2H,t,J=6.2 Hz), 4.15(2H,t,J=6.2 Hz),

[0146] 4.96(2H,s), 7.18(1H,d,J=8.4 Hz),

[0147] 7.46(1H,d,J=8.4 Hz), 7.90(1H,s).

[0148] (13). N-(3-chloro-2,6-diethylphenyl)-2,3-quinoxaline-dicarboximide

[0149]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0150] 1.11(3H,t,J=7.5 Hz), 1.16(3H,t,J=7.5 Hz),

[0151] 2.46(2H,q,J=7.5 Hz), 2.64(2H,q,J=7.5 Hz),

[0152] 7.24(1H,d,J=8.4 Hz), 7.51(1H,d,J=8.4 Hz), 8.07-8.13(2H,m), 8.48-8.54(2H,m).

[0153] (14). N-(3-chloro-2-methylphenyl)-2,3-quinoxaline-dicarboximide

[0154]¹H-NMR [TMS/CDC₃, δ (ppm)]

[0155] 2.29(3H,s), 7.24(1H,d,J=8.0 Hz),

[0156] 7.34(1H,t,J=8.0 Hz), 7.56(1H,d,J=8.0 Hz), 8.06-8.12(2H,m), 8.46-8.51(2H,m).

[0157] (15). N-(3-chloro-2,6-diethylphenyl)-5-fluoro-2,3-quinolinedicarboximide

[0158] mp 116-118° C.

[0159] (16). N-(3-chloro-2,6-diethylphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0160]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0161] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz),

[0162] 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m),

[0163] 7.22(1H,d,J=8.1 Hz), 7.48(1H,d,J=8.1 Hz), 7.75-7.81(2H,m), 8.51(1H,m), 8.77(1H,s).

[0164] (17). N-(3-chloro-2,6-diethylphenyl)-7-fluoro-2,3-quinolinedicarboximide

[0165]¹H-NMR [TMS/CDCl₃δ (ppm)]

[0166] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.5 Hz),

[0167] 2.44(2H,q,J=7.5 Hz), 2.56-2.68(2H,m),

[0168] 7.22(1H,d,J=8.1 Hz), 7.48(1H,d,J=8.1 Hz),

[0169] 7.63(1H,ddd,J=2.4, 8.1 and 9.3 Hz),

[0170] 8.12(1H,dd,J=2.4 and 9.6 Hz), 8.16(1H,dd,J=5.7 and

[0171] 9.3 Hz), 8.81(1H,s).

[0172] (18). N-(4-trifluoromethoxyphenyl)-7-fluoro-2,3-quinolinedicarboximide

[0173] mp 264-266° C.

[0174] (19). N-(4-trifluoromethoxyphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0175] mp 287-289° C.

[0176] (20). N-(4-trifluoromethoxyphenyl)-5-fluoro-2,3-quinolinedicarboximide

[0177]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0178] 7.39-7.43(2H,m), 7.51(1H,ddd,J=0.9, 7.8 and

[0179] 9.0 Hz), 7.63-7.80(2H,m), 7.95(1H,ddd,J=6.0, 7.8 and 8.4 Hz), 8.30(1H,dd,J=0.9 and 8.4 Hz),

[0180] 9.09(1H,d,J=0.9 Hz).

[0181] (21). N-(2-methyl-4-pentafluoroethylphenyl)-6-fluoro-2,3-quinolinedicarboximide

[0182]¹H-NMR [TMS/CDC₃, δ (ppm)]

[0183] 2.33(3H,s), 7.43(1H,d,J=8.4 Hz),

[0184] 7.62(1H,d,J=8.4 Hz), 7.64(1H,s), 7.81-7.72(2H,m),

[0185] 8.50(1H,dd,J=5.4 and 9.0 Hz), 8.77(1H,s).

[0186] (22). N-(3-chloro-2,6-diethylphenyl)-5-chloro-2,3-quinolinedicarboximide

[0187]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0188] 1.10(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz),

[0189] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0190] 7.22(1H,d,J=8.5 Hz), 7.50(1H,d,J=8.5 Hz), 7.89-7.96(2H,m), 8.42(1H,dd,J=2.0 and 8.0 Hz),

[0191] 9.29(1H,s).

[0192] (23). N-(3-chloro-2,6-diethylphenyl)-6-chloro-2,3-quinolinedicarboximide

[0193]¹H-NMR [TMS/d₆-DMSO, δ (ppm)]

[0194] 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz),

[0195] 2.40(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz),

[0196] 7.36(1H,d,J=8.5 Hz), 7.61(1H,d,J=8.5 Hz),

[0197] 8.09(1H,d,J=8.1 Hz), 8.40(1H,d,J=8.1 Hz),

[0198] 8.52(1H,s), 9.15(1H,s).

[0199] (24). N-(3-chloro-methylphenyl)-6-chloro-2,3-quinolinedicarboximide

[0200]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0201] 2.27(3H,s), 7.20(1H,d,J=7.8 Hz),

[0202] 7.32(1H,t,J=7.8 Hz), 7.53(1H,d,J=7.8 Hz),

[0203] 7.93(1H,dd,J=2.0 and 8.0 Hz), 8.11(1H,d,J=2.0 Hz),

[0204] 8.42(1H,d,J=8.0 Hz), 8.71(1H,s).

[0205] (25). N-(3-chloro-2,6-diethylphenyl)-7-chloro-2,3-quinolinedicarboximide

[0206]¹H-NMR [TMS/d₆-DMSO, δ (ppm)]

[0207] 0.99(3H,t,J=7.5 Hz), 1.04(3H,t,J=7.5 Hz),

[0208] 2.45(2H,q,J=7.5 Hz), 2.61(2H,q,J=7.5 Hz),

[0209] 7.37(1H,d,J=8.5 Hz), 7.62(1H,d,J=8.5 Hz),

[0210] 7.99(1H,dd,J=2.5 and 8.5 Hz), 8.43(1H,d,J=8.5 Hz),

[0211] 8.48(1H,d,J=2.5 Hz), 9.24(1H,s).

[0212] (26). N-(3-chloro-2,6-diethylphenyl)-5-methyl-2,3-quinolinedicarboximide

[0213] mp 178-180° C.

[0214] (27). N-(3-chloro-2,6-diethylphenyl)-6-methyl-2,3-quinolinedicarboximide

[0215]¹H-NMR [TMS/CDCl₃δ (ppm)]

[0216] 1.10(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0217] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0218] 2.65(3H,s), 7.21(1H,d,J=8.5 Hz),

[0219] 7.47(1H,d,J=8.5 Hz), 7.80(1H,d,J=8.0 Hz),

[0220] 7.88(1H,s), 8.37(1H,d,J=8.0 Hz), 8.71(1H,s).

[0221] (28). N-(3-chloro-2,6-diethylphenyl)-8-methyl-2,3-quinolinedicarboximide

[0222]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0223] 1.00(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0224] 2.45(2H,q,J=7.5 Hz), 2.60(2H,q,J=7.5 Hz),

[0225] 2.95(3H,s), 7.20(1H,d,J=8.5 Hz),

[0226] 7.40(1H,d,J=8.5 Hz), 7.70(1H,t,J=8.0 Hz),

[0227] 7.95(1H,d,J=8.0 HZ), 8.75(1H,s).

[0228] (29). N-(3-chloro-2-methylphenyl)-6-methyl-2,3-quinolinedicarboximide

[0229]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0230] 2.26(3H,s), 2.65(3H,s), 7.20(1H,d,J=8.5 Hz),

[0231] 7.30(1H,t,J=8.5 Hz), 7.51(1H,d,J=8.5 Hz),

[0232] 7.85(1H,d,J=8.0 Hz), 7.87(1H,s),

[0233] 8.35(1H,d,J=8.0 Hz), 8.69(1H,s).

[0234] (30). N-(3-chloro-2,6-diethylphenyl)-6-hydroxy-2,3-quinolinedicarboximide

[0235]¹H-NMR [TMS/CDCl₃, 6 (ppm)]

[0236] 1.06(3H,t,J=7.5 Hz), 1.14(3H,t,J=7.5 Hz),

[0237] 2.45(2H,q,J=7.5 Hz), 2.65(2H,q,J=7.5 Hz),

[0238] 7.20(1H,d,J=8.0 Hz), 7.45(1H,d,J=1.1 Hz), 7.50(1H,d,J=8.0 Hz), 7.60(1H,dd,J=1.1 and 8.5 Hz),

[0239] 8.38(1H,d,J=8.5 Hz), 8.62(1H,s).

[0240] (31). N-(3-chloro-2,6-diethylphenyl)-6-methoxy-2,3-quinolinedicarboximide

[0241]¹H-NMR [TMS/d6-DMSO, δ (ppm)]

[0242] 1.10(3H,t,J=7.5 Hz), 1.18(3H,t,J=7.5 Hz),

[0243] 2.50(2H,q,J=7.5 Hz), 2.87(2H,q,J=7.5 Hz),

[0244] 3.95(1H,s), 7.21(1H,d,J=8.5 Hz),

[0245] 7.35(1H,d,J=8.5 Hz), 8.05(1H,d,J=8.0 Hz),

[0246] 8.86(1H,s), 9.24(1H,s), 10.28(1H,d,J=8.0 Hz).

[0247] (32). N-(3-chloro-2,6-diethylphenyl)-6,7-dimethoxy-2,3-quinolinedicarboximide

[0248]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0249] 1.09(3H,t,J=7.8 Hz), 1.14(3H,t,J=7.8 Hz),

[0250] 2.45(2H,q,J=7.8 Hz), 2.63(2H,q,J=7.8 Hz),

[0251] 4.10(6H,s), 7.20(1H,d,J=8.5 Hz), 7.28(1H,s),

[0252] 7.45(1H,d,J=8.5 Hz), 7.76(1H,s), 8.58(1H,s).

[0253] (33). N-(3-chloro-2,6-diethylphenyl)-6,7-methylenedioxy-2,3-quinolinedicarboximide

[0254]¹H-NMR [TMS/CDCl₃, δ (ppm)]

[0255] 1.09(3H,t,J=7.5 Hz), 1.15(3H,t,J=7.5 Hz),

[0256] 2.45(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0257] 6.27(2H,s), 7.20(1H,d,J=8.5 Hz), 7.32(1H,s),

[0258] 7.45(1H,d,J=8.5 Hz), 7.71(1H,s), 8.55(1H,s).

[0259] The fused heterocyclic diesters represented by general formula (VIII) and the dicarboxylic acids represented by general formula (VII) can be produced according to known methods, for example, the methods described in U.S. Pat. No. 3,414,580, U.S. Pat. No. 3,686,171, J. Med. Chem., 27, 1396 (1984), J. Heterocyclic Chem., 12, 1303 (1975), ibid. 15, 1447 (1978), ibid. 16, 1141 (1979), ibid. 17, 443 (1982), ibid. 21, 689 (1984), Beil., 25III, 2028, JP-A-52-77086, J. Am. Chem. Soc. , 81, 2456 (1956), J. Org. Chem., 37, 3224 (1972), JP-A-62-175480, JP-A-62-230782, JP-A-60-69083, JP-A-60-185783, JP-A-61-109790, JP-A-62-277385, JP-A-63-295575, JP-A-63-99067, JP-A-64-75474, JP-A-64-90118, Yakugaku Zasshi, 84, 416 (1964), Chem. and Pharm. Bull., 5, 277 (1957), J. Chem. Research (S), 1989, 196, etc.

[0260] E. General Formula (III)→General Formula (I-1)

[0261] As the inert solvents usable in this reaction, the inert solvents exemplified in B and pyridines can be referred to.

[0262] Since this reaction is an equimolar reaction, an amine represented by general formula (II-1) or an amine salt represented by general formula (II-2) is used in an equimolar amount to an imide represented by general formula (III), or in an excessive amount, if desired.

[0263] When an amine salt represented by general formula (II-2) is used in this reaction, a base must be used for the purpose of generating a free amine in the reaction system. As the base, an inorganic amine or an organic amine can be used. As the inorganic amine, for example, alkali metal hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and the like can be used. As the organic base, for example, triethylamine, pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo-[5,4,0]-7-undecene and the like can be used. The amount of these amines may be appropriately selected from a range of an equimolar amount to an excessive molar amount.

[0264] The reaction temperature may be appropriately selected from a range of −10° C. to the boiling point range of the used inert solvent, and preferably from a range of 0° C. to 150° C.

[0265] The reaction time may vary with temperature and scale of the reaction, and it ranges from several minutes to 48 hours.

[0266] After completion of the reaction, the objective product is isolated from the reaction system containing it and purified by recrystallization, distillation, column chromatography, etc. according to the need, whereby the objective product can be obtained.

[0267] Hereunder, typical examples of the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) and salt thereof will be shown in Table 1 to Table 14. The present invention is by no means limited by these compounds. In the tables, the expression “c-” means an alicyclic hydrocarbon, and the expression “Het” means

TABLE 1

No Y R³ X R⁴ mp ° C.  1 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 5-CH₃ 188-190  2 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-CH₃ 208-210  3 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-CH₃ 190-192  4 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  5 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  6 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  7 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  8 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  9 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  10 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  11 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  12 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  13 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 5-CH₃  14 H CH₃ 2-CH₃-3-Cl 5-CH₃  15 H C₂H₅ 2-CH₃-3-Cl 5-CH₃  16 H n-C₃H₇ 2-CH₃-3-Cl 5-CH₃  17 H i-C₃H₇ 2-CH₃-3-Cl 5-CH₃  18 H c-C₃H₅ 2-CH₃-3-Cl 5-CH₃  19 H n-C₄H₉ 2-CH₃-3-Cl 5-CH₃  20 H s-C₄H₉ 2-CH₃-3-Cl 5-CH₃  21 H i-C₄H₉ 2-CH₃-3-Cl 5-CH₃  22 H t-C₄H₉ 2-CH₃-3-Cl 5-CH₃  23 H n-C₅H₁₁ 2-CH₃-3-Cl 5-CH₃  24 H neo-C₅H₁₁ 2-CH₃-3-Cl 5-CH₃  25 H c-C₅H₉ 2-CH₃-3-Cl 5-CH₃  26 H t-C₅H₁₁ 2-CH₃-3-Cl 5-CH₃  27 H n-C₆H₁₃ 2-CH₃-3-Cl 5-CH₃  28 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 234-236  29 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 226-228  30 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 221-222  31 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  32 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  33 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  34 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  35 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  36 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  37 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  38 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  39 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  40 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  41 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6-CH₃  42 H CH₃ 2-CH₃-3-Cl 6-CH₃  43 H C₂H₅ 2-CH₃-3-Cl 6-CH₃ 225-228  44 H n-C₃H₇ 2-CH₃-3-Cl 6-CH₃ 217-220  45 H i-C₃H₇ 2-CH₃-3-Cl 6-CH₃  46 H c-C₃H₅ 2-CH₃-3-Cl 6-CH₃  47 H n-C₄H₉ 2-CH₃-3-Cl 6-CH₃  48 H s-C₄H₉ 2-CH₃-3-Cl 6-CH₃  49 H i-C₄H₉ 2-CH₃-3-Cl 6-CH₃  50 H t-C₄H₉ 2-CH₃-3-Cl 6-CH₃  51 H n-C₅H₁₁ 2-CH₃-3-Cl 6-CH₃  52 H neo-C₅H₁₁ 2-CH₃-3-Cl 6-CH₃  53 H c-C₅H₉ 2-CH₃-3-Cl 6-CH₃ 218-219  54 H C₂H₅ 4-OCF₃ 6-CH₃ 215-217  55 H n-C₃H₇ 4-OCF₃ 6-CH₃ 202-204  56 H i-C₃H₇ 4-OCF₃ 6-CH₃ 213-215  57 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  58 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-CH₃ 199-201  59 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  60 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  61 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  62 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  63 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  64 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  65 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  66 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  67 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  68 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  69 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 7-CH₃  70 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  71 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 8-CH₃ 227-228  72 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  73 H c-C₃H₆ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  74 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  75 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  76 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  77 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  78 H n-C₅H₁₁ 2,6-(C₂H₅)₂3-Cl 8-CH₃  79 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  80 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  81 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  82 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 8-CH₃  83 H CH₃ 2-CH₃-3-Cl 8-CH₃  84 H C₂H₅ 2-CH₃-3-Cl 8-CH₃  85 H n-C₃H₇ 2-CH₃-3-Cl 8-CH₃  86 H i-C₃H₇ 2-CH₃-3-Cl 8-CH₃  87 H c-C₃H₅ 2-CH₃-3-Cl 8-CH₃  88 H n-C₄H₉ 2-CH₃-3-Cl 8-CH₃  89 H s-C₄H₉ 2-CH₃-3-Cl 8-CH₃  90 H i-C₄H₉ 2-CH₃-3-Cl 8-CH₃  91 H t-C₄H₉ 2-CH₃-3-Cl 8-CH₃  92 H n-C₅H₁₁ 2-CH₃-3-Cl 8-CH₃  93 H neo-C₅H₁₁ 2-CH₃-3-Cl 8-CH₃  94 H c-C₅H₉ 2-CH₃-3-Cl 8-CH₃  95 H t-C₅H₁₁ 2-CH₃-3-Cl 8-CH₃  96 H n-C₆H₁₃ 2-CH₃-3-Cl 8-CH₃  97 H H 2,6-(C₂H₅)₂-3-Cl 5-F 266-268  98 H CH₃ 2,6-(C₂H₅)₂-3-Cl 5-F  99 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 5-F 227-229 100 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-F 207-209 101 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-F 213-215 102 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 5-F 103 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-F 104 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-F 105 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-F 106 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-F 107 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-F 108 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-F 109 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 5-F 110 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-F 111 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 5-F 112 H CH₃ 2-CH₃-3-Cl 5-F 113 H C₂H₅ 2-CH₃-3-Cl 5-F 114 H n-C₃H₇ 2-CH₃-3-Cl 5-F 115 H i-C₃H₇ 2-CH₃-3-Cl 5-F 116 H c-C₃H₅ 2-CH₃-3-Cl 5-F 117 H n-C₄H₉ 2-CH₃-3-Cl 5-F 118 H s-C₄H₉ 2-CH₃-3-Cl 5-F 119 H i-C₄H₉ 2-CH₃-3-Cl 5-F 120 H t-C₄H₉ 2-CH₃-3-Cl 5-F 121 H n-C₅H₁₁ 2-CH₃-3-Cl 5-F 122 H neo-C₅H₁₁ 2-CH₃-3-Cl 5-F 123 H c-C₅H₉ 2-CH₃-3-Cl 5-F 124 H n-C₃H₇ 4-OCF₃ 5-F 191-193 125 H i-C₃H₇ 4-OCF₃ 5-F 210-212 126 H H 2,6-(C₂H₅)₂-3-Cl 6-F 286-288 127 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6-F 247-249 128 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-F 212-213 129 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-F 210-212 130 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-F 202-204 131 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-F 132 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-F 133 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-F 134 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-F 135 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-F 136 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-F 137 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-F 138 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-F 139 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-F 140 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6-F 141 H CH₃ 2-CH₃-3-Cl 6-F 142 H C₂H₅ 2-CH₃-3-Cl 6-F 143 H n-C₃H₇ 2-CH₃-3-Cl 6-F 144 H i-C₃H₇ 2-CH₃-3-Cl 6-F 145 H c-C₃H₅ 2-CH₃-3-Cl 6-F 146 H n-C₄H₉ 2-CH₃-3-Cl 6-F 147 H s-C₄H₉ 2-CH₃-3-Cl 6-F 148 H i-C₄H₉ 2-CH₃-3-Cl 6-F 149 H t-C₄H₉ 2-CH₃-3-Cl 6-F 150 H n-C₅H₁₁ 2-CH₃-3-Cl 6-F 151 H neo-C₅H₁₁ 2-CH₃-3-Cl 6-F 152 H c-C₅H₉ 2-CH₃-3-Cl 6-F 153 H t-C₅H₁₁ 2-CH₃-3-Cl 6-F 154 H n-C₆H₁₃ 2-CH₃-3-Cl 6-F 155 H C₂H₅ 4-OCF₃ 6-F 242-244 156 H i-C₃H₇ 4-OCF₃ 6-F 248-250 157 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 7-F 231-233 158 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-F 220-222 159 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-F 160 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 7-F 161 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-F 162 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-F 163 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-F 164 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-F 165 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-F 166 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-F 167 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 7-F 168 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-F 169 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 7-F 170 H CH₃ 2-CH₃-3-Cl 7-F 171 H C₂H₅ 2-CH₃-3-Cl 7-F 172 H n-C₃H₇ 2-CH₃-3-Cl 7-F 173 H i-C₃H₇ 2-CH₃-3-Cl 7-F 174 H c-C₃H₅ 2-CH₃-3-Cl 7-F 175 H n-C₄H₉ 2-CH₃-3-Cl 7-F 176 H s-C₄H₉ 2-CH₃-3-Cl 7-F 177 H i-C₄H₉ 2-CH₃-3-Cl 7-F 178 H t-C₄H₉ 2-CH₃-3-Cl 7-F 179 H n-C₅H₁₁ 2-CH₃-3-Cl 7-F 180 H neo-C₅H₁₁ 2-CH₃-3-Cl 7-F 181 H c-C₅H₉ 2-CH₃-3-Cl 7-F 182 H t-C₅H₁₁ 2-CH₃-3-Cl 7-F 183 H n-C₆H₁₃ 2-CH₃-3-Cl 7-F 184 H C₂H₅ 4-OCF₃ 7-F 269-271 185 H i-C₃H₇ 4-OCF₃ 7-F 264-266 186 H H 2,6-(C₂H₅)₂-3-Cl 5-Cl 187 H CH₃ 2,6-(C₂H₅)₂-3-Cl 5-Cl 188 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 5-Cl 189 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-Cl 235-237 190 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 5-Cl 191 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 5-Cl 192 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-Cl 193 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-Cl 194 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-Cl 195 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 5-Cl 196 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-Cl 197 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-Cl 198 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 5-Cl 199 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 5-Cl 200 H CH₂CH₂CN 2,6-(C₂H₅)₂-3-Cl 5-Cl 217-219 201 H CH₂CH₂OCH₃ 2,6-(C₂H₅)₂-3-Cl 5-Cl 199-201 202 H CH₃ 2-CH₃-3-Cl 5-Cl 203 H C₂H₅ 2-CH₃-3-Cl 5-Cl 204 H n-C₃H₇ 2-CH₃-3-Cl 5-Cl 205 H i-C₃H₇ 2-CH₃-3-Cl 5-Cl 206 H c-C₃H₅ 2-CH₃-3-Cl 5-Cl 207 H n-C₄H₉ 2-CH₃-3-Cl 5-Cl 208 H s-C₄H₉ 2-CH₃-3-Cl 5-Cl 209 H i-C₄H₉ 2-CH₃-3-Cl 5-Cl 210 H t-C₄H₉ 2-CH₃-3-Cl 5-Cl 211 H n-C₅H₁₁ 2-CH₃-3-Cl 5-Cl 212 H neo-C₅H₁₁ 2-CH₃-3-Cl 5-Cl 213 H c-C₅H₉ 2-CH₃-3-Cl 5-Cl 214 H n-C₃H₇ 4-OCF₃ 5-Cl 210-212 215 H i-C₃H₇ 4-OCF₃ 5-Cl 228-229 216 H H 2,6-(C₂H₅)₂-3-Cl 6-Cl 217 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6-Cl 218 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-Cl 219 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-Cl 211-213 220 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-Cl 221 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-Cl 222 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 223 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 224 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 214-215 225 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 226 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl 227 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl 228 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 203-204 229 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl 230 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6-Cl 231 H CH₃ 2-CH₃-3-Cl 6-Cl 232 H C₂H₅ 2-CH₃-3-Cl 6-Cl 234 H n-C₃H₇ 2-CH₃-3-Cl 6-Cl 217-219 235 H i-C₃H₇ 2-CH₃-3-Cl 6-Cl 236 H c-C₃H₅ 2-CH₃-3-Cl 6-Cl 237 H n-C₄H₉ 2-CH₃-3-Cl 6-Cl 238 H s-C₄H₉ 2-CH₃-3-Cl 6-Cl 239 H i-C₄H₉ 2-CH₃-3-Cl 6-Cl 240 H t-C₄H₉ 2-CH₃-3-Cl 6-Cl 241 H n-C₅H₁₁ 2-CH₃-3-Cl 6-Cl 242 H neo-C₅H₁₁ 2-CH₃-3-Cl 6-Cl 243 H c-C₅H₉ 2-CH₃-3-Cl 6-Cl 236-238 244 H t-C₅H₁₁ 2-CH₃-3-Cl 6-Cl 245 H n-C₆H₁₃ 2-CH₃-3-Cl 6-Cl 246 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 7-Cl 238-240 247 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-Cl 248 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 7-Cl 249 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 7-Cl 250 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-Cl 251 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-Cl 252 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-Cl 253 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 7-Cl 254 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-Cl 255 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-Cl 256 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 7-Cl 257 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 7-Cl 258 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 7-Cl 259 H CH₃ 2-CH₃-3-Cl 7-Cl 260 H C₂H₅ 2-CH₃-3-Cl 7-Cl 261 H n-C₃H₇ 2-CH₃-3-Cl 7-Cl 262 H i-C₃H₇ 2-CH₃-3-Cl 7-Cl 263 H c-C₃H₅ 2-CH₃-3-Cl 7-Cl 264 H n-C₄H₉ 2-CH₃-3-Cl 7-Cl 265 H s-C₄H₉ 2-CH₃-3-Cl 7-Cl 266 H i-C₄H₉ 2-CH₃-3-Cl 7-Cl 267 H t-C₄H₉ 2-CH₃-3-Cl 7-Cl 268 H n-C₅H₁₁ 2-CH₃-3-Cl 7-Cl 269 H neo-C₅H₁₁ 2-CH₃-3-Cl 7-Cl 270 H c-C₅H₉ 2-CH₃-3-Cl 7-Cl 271 H t-C₅H₁₁ 2-CH₃-3-Cl 7-Cl 272 H n-C₆H₁₃ 2-CH₃-3-Cl 7-Cl 273 H H 2,6-(C₂H₅)₂-3-Cl 6-OH 274 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6-OH 275 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-OH 239-241 276 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-OH 266-267 277 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-OH 278 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-OH 279 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OH 280 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OH 281 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OH 282 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OH 283 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OH 284 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OH 285 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-OH 286 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OH 287 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6-OH 288 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 289 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 209-210 290 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 173-175 291 H i-C₃H₇O 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 178-181 292 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 293 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 294 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 295 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 296 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 297 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 298 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 299 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 300 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 301 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6-OCH₃ 302 H H 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 303 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 304 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 305 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 223-225 306 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 307 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 308 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 309 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 310 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 204-206 311 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 312 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 313 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 314 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 315 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 316 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6,7-(OCH₃)₂ 317 H CH₃ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 318 H C₂H₅ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 319 H n-C₃H₇ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 320 H i-C₃H₇ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 321 H c-C₃H₅ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 322 H n-C₄H₉ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 323 H s-C₄H₉ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 324 H i-C₄H₉ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 325 H t-C₄H₉ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 326 H n-C₅H₁₁ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 327 H neo-C₅H₁₁ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 328 H c-C₅H₉ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 329 H t-C₅H₁₁ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 330 H n-C₆H₁₃ 2-CH₃-3-Cl 6,7-(OCH₃)₂ 331 H H 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 332 H CH₃ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 333 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 334 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6,7- 213-215 (OCH₂O) 335 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 336 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 337 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 338 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 339 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7- 221-223 (OCH₂O) 340 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 341 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 342 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 343 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6,7- 191-193 (OCH₂O) 344 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 345 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl 6,7- (OCH₂O) 346 H CH₃ 2-CH₃-3-Cl 6,7- (OCH₂O) 347 H C₂H₅ 2-CH₃-3-Cl 6,7- (OCH₂O) 348 H n-C₃H₇ 2-CH₃-3-Cl 6,7- (OCH₂O) 349 H i-C₃H₇ 2-CH₃-3-Cl 6,7- (OCH₂O) 350 H c-C₃H₅ 2-CH₃-3-Cl 6,7- (OCH₂O) 351 H n-C₄H₉ 2-CH₃-3-Cl 6,7- (OCH₂O) 352 H s-C₄H₉ 2-CH₃-3-Cl 6,7- (OCH₂O) 353 H i-C₄H₉ 2-CH₃-3-Cl 6,7- (OCH₂O) 354 H t-C₄H₉ 2-CH₃-3-Cl 6,7- (OCH₂O) 355 H n-C₅H₁₁ 2-CH₃-3-Cl 6,7- (OCH₂O) 356 H neo-C₅H₁₁ 2-CH₃-3-Cl 6,7- (OCH₂O) 357 H c-C₅H₉ 2-CH₃-3-Cl 6,7- (OCH₂O) 358 H t-C₅H₁₁ 2-CH₃-3-Cl 6,7- (OCH₂O) 359 H n-C₆H₁₃ 2-CH₃-3-Cl 6,7- (OCH₂O) 359-1 H CH₃ 2,6-(C₂H₅)₂-3-Cl H 235-237 359-2 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl H 205-207 359-3 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H 211-213 359-4 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H 195-197 359-5 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H 141-143 359-6 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H 161-163

[0268] TABLE 2

No R² R³ X A E mp ° C. 360 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl N CH 249-264 361 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl N CH 234-250 362 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl N CH 363 H c-C₃H₇ 2,6-(C₂H₅)₂-3-Cl N CH 364 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N CH 365 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N CH 366 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N CH 367 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N CH 368 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N CH 369 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N CH 370 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl N CH 371 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N CH 372 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl N CH 373 H CH₃ 2-CH₃-3-Cl N CH 374 H C₂H₅ 2-CH₃-3-Cl N CH 375 H n-C₃H₇ 2-CH₃-3-Cl N CH 223-245 376 H i-C₃H₇ 2-CH₃-3-Cl N CH 377 H c-C₃H₅ 2-CH₃-3-Cl N CH 378 H n-C₄H₉ 2-CH₃-3-Cl N CH 379 H s-C₄H₉ 2-CH₃-3-Cl N CH 380 H i-C₄H₉ 2-CH₃-3-Cl N CH 381 H t-C₄H₉ 2-CH₃-3-Cl N CH 382 H n-C₅H₁₁ 2-CH₃-3-Cl N CH 383 H neo-C₅H₁₁ 2-CH₃-3-Cl N CH 384 H c-C₅H₉ 2-CH₃-3-Cl N CH 385 H t-C₅H₁₁ 2-CH₃-3-Cl N CH 386 H n-C₆H₁₃ 2-CH₃-3-Cl N CH 387 H C₂H₅ 2,6-(C₂H₅)₂-3-Cl N N 388 H n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl N N 215-220 389 H i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl N N 390 H c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl N N 391 H n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N N 392 H s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N N 393 H i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N N 394 H t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl N N 395 H n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N N 396 H neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N N 397 H c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl N N 398 H t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl N N 399 H n-C₆H₁₃ 2,6-(C₂H₅)₂-3-Cl N N 400 H CH₃ 2-CH₃-3-Cl N N 401 H C₂H₅ 2-CH₃-3-Cl N N 402 H n-C₃H₇ 2-CH₃-3-Cl N N 403 H i-C₃H₇ 2-CH₃-3-Cl N N 404 H c-C₃H₅ 2-CH₃-3-Cl N N 405 H n-C₄H₉ 2-CH₃-3-Cl N N 406 H s-C₄H₉ 2-CH₃-3-Cl N N 407 H i-C₄H₉ 2-CH₃-3-Cl N N 408 H t-C₄H₉ 2-CH₃-3-Cl N N 409 H n-C₅H₁₁ 2-CH₃-3-Cl N N 410 H neo-C₅H₁₁ 2-CH₃-3-Cl N N 411 H c-C₅H₉ 2-CH₃-3-Cl N N 412 H t-C₅H₁₁ 2-CH₃-3-Cl N N

[0269] TABLE 3

No R³ X F G J K mp ° C. 413 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 414 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 188-191 415 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 416 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 417 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 418 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 419 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 420 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 421 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 422 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 423 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 185-189 424 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CH₂ 425 C₂H₅ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 426 n-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 427 i-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 428 c-C₃H₅ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 429 n-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 430 s-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 431 i-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 180-183 432 t-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 433 n-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 434 neo-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 435 c-C₅H₉ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 436 t-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CH₂ 437 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 438 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 190-194 439 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 440 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 441 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 442 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 443 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 444 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 445 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 446 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 447 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 187-190 448 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ CH₂ 449 C₂H₅ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 450 n-C₃H₇ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 188-190 451 i-C₃H₇ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 452 c-C₃H₅ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 453 n-C₄H₉ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 454 s-C₄H₉ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 455 i-C₄H₉ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 456 t-C₄H₉ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 457 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 458 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 459 c-C₅H₉ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 460 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ O CH₂ CH₂ 461 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 462 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 166-170 463 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 464 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 465 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 466 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 467 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 468 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 469 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 470 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 471 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 472 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O CH₂ 473 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 474 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 168-171 475 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 476 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 477 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 478 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 479 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 480 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 481 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 482 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 483 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 484 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O CH₂ 485 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 486 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 194-196 487 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 488 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 489 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 490 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 491 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 492 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 493 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 494 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 495 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 496 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ O 497 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 498 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 195-198 499 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 500 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 501 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 502 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 503 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 504 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 505 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 506 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 507 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 508 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ O 509 C₂H₅ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 510 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 181-183 511 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 512 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 513 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 514 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 515 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 516 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 517 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 518 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 519 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 175-180 520 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ CH₂ 521 C₂H₅ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 522 n-C₃H₇ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 523 i-C₃H₇ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 524 c-C₃H₅ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 525 n-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 526 s-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 527 i-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 178-181 528 t-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 529 n-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 530 neo-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 531 c-C₅H₉ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 532 t-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ CH₂ 533 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 534 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 180-184 535 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 536 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 537 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 538 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 539 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 540 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 541 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 542 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 543 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 544 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ S CH₂ CH₂ 545 C₂H₅ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 546 n-C₃H₇ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 547 i-C₃H₇ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 548 c-C₃H₅ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 549 n-C₄H₉ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 550 s-C₄H₉ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 551 i-C₄H₉ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 552 t-C₄H₉ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 553 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 554 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 555 c-C₅H₉ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 556 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ S CH₂ CH₂ 557 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 558 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 179-180 559 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 560 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 561 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 562 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 563 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 564 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 565 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 566 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 567 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 568 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S CH₂ 569 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 570 n-C₃H₇ 2-CH₂-3-Cl CH₂ CH₂ S CH₂ 182-185 571 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 572 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 573 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 574 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 575 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 576 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 577 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 578 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 579 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 580 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ S CH₂ 581 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 582 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 186-190 583 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 584 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 585 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 586 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 587 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 588 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 589 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 590 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 591 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 592 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ S 593 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 594 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 595 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 596 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 597 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 598 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 599 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 600 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₃ CH₂ S 601 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 602 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 603 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 604 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ S 605 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 606 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂  93-100 607 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 608 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 609 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 610 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 611 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 612 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 613 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 614 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 615 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 616 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO CH₂ 617 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 618 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 619 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 620 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 621 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 622 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 623 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 624 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 625 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 626 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 627 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 628 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO CH₂ 629 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 630 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 86-96 631 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 632 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 633 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 634 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 635 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 636 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 637 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 638 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 639 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 640 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ CH₂ 641 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 642 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 643 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 644 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 645 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 646 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 647 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 648 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 649 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 650 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 651 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 652 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ SO₂ CH₂ 653 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 654 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ Refractive index 1.4764 (20° C.) 655 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 656 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 657 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 658 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 659 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 660 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 661 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 662 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 663 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 664 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ CH₂ 665 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 667 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 668 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 669 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 670 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 671 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 672 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 673 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 674 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 675 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 676 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 677 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ NCH₃ CH₂ 678 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 212-213 679 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 214-215 680 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 681 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 682 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 683 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 684 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 685 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 686 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 687 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 688 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 689 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ CH₂ CO 690 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 691 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 692 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 693 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 694 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 695 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 696 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 697 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 698 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 699 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 700 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 701 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ CH₂ CO 702 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 703 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 185-188 704 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 705 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 706 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 707 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 708 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 709 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 710 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 711 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 712 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 713 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ CO 714 C₂H₅ 2-CH₃-3-Cl O CH₂ CH₂ CO 715 n-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ CO 716 i-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ CO 717 c-C₃H₅ 2-CH₃-3-Cl O CH₂ CH₂ CO 718 n-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CO 719 s-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CO 720 i-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CO 721 t-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ CO 722 n-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CO 723 neo-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CO 724 c-C₅H₉ 2-CH₃-3-Cl O CH₂ CH₂ CO 189-192 725 t-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ CO 726 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 727 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 198-201 728 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 729 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 730 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 731 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 732 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 733 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 734 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 735 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 736 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 737 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH═CH CO 738 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 739 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 173-175 740 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 741 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 742 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 743 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 744 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 745 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 746 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 747 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 748 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 749 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ O 750 C₂H₅ 2-CH₃-3-Cl O CH₂ CH₂ O 751 n-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ O 752 i-C₃H₇ 2-CH₃-3-Cl O CH₂ CH₂ O 753 c-C₃H₅ 2-CH₃-3-Cl O CH₂ CH₂ O 754 n-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ O 755 s-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ O 756 i-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ O 757 t-C₄H₉ 2-CH₃-3-Cl O CH₂ CH₂ O 758 n-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ O 759 neo-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ O 760 c-C₅H₉ 2-CH₃-3-Cl O CH₂ CH₂ O 179-182 761 t-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ O 762 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 763 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 153-155 764 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 765 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 766 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 767 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 768 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 769 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 770 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 771 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 772 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃ 773 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ NCH₃

[0270] TABLE 4

No R³ X (R⁹)_(m) Z mp ° C. 774 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H O 226-229 775 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 192-193 776 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 777 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H O 778 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 779 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 780 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 781 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 782 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 783 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 784 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H O 785 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 786 C₂H₅ 2-CH₃-3-Cl H O 787 n-C₃H₇ 2-CH₃-3-Cl H O 788 i-C₄H₉ 2-CH₃-3-Cl H O 789 c-C₃H₅ 2-CH₃-3-Cl H O 790 n-C₄H₉ 2-CH₃-3-Cl H O 791 s-C₄H₉ 2-CH₃-3-Cl H O 792 i-C₄H₉ 2-CH₃-3-Cl H O 793 t-C₄H₉ 2-CH₃-3-Cl H O 794 n-C₅H₁₁ 2-CH₃-3-Cl H O 795 neo-C₅H₁₁ 2-CH₃-3-Cl H O 796 c-C₅H₉ 2-CH₃-3-Cl H O 198-200 797 t-C₅H₁₁ 2-CH₃-3-Cl H O 798 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H S 225-229 799 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 194-196 800 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 801 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H S 802 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 803 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 804 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 805 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 806 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 807 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 808 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H S 809 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 810 neo-C₅H₁₁ 2-CH₃-3-Cl H S 811 c-C₅H₉ 2-CH₃-3-Cl H S 197-199 812 t-C₅H₁₁ 2-CH₃-3-Cl H S 813 C₂H₅ 2,6-(C₂H₅)₂-3-Cl 3-Br S 814 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 3-Br S 187-190 815 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 3-Br S 816 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 3-Br S 817 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 3-Br S 818 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 3-Br S 819 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 3-Br S 820 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 3-Br S 821 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 3-Br S 822 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 3-Br S 823 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 824 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 166-169 825 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 826 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 827 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 828 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 829 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 830 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 831 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 832 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 833 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 834 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃

[0271] TABLE 5

No R³ X (R⁹)_(m) Z mp ° C. 835 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H S 836 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 837 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 198-201 838 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H S 839 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 840 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 841 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 842 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 843 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 844 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 845 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H S

[0272] TABLE 6

No R³ X (R⁹)_(m) Z mp ° C. 846 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H O 847 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 198-201 848 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 849 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H O 850 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 851 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 852 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 853 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 854 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 855 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 856 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H O 857 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 858 C₂H₅ 2-CH₃-3-Cl H O 859 n-C₃H₇ 2-CH₃-3-Cl H O 860 i-C₃H₇ 2-CH₃-3-Cl H O 861 c-C₃H₅ 2-CH₃-3-Cl H O 862 n-C₄H₉ 2-CH₃-3-Cl H O 863 s-C₄H₉ 2-CH₃-3-Cl H O 864 i-C₄H₉ 2-CH₃-3-Cl H O 865 t-C₄H₉ 2-CH₃-3-Cl H O 866 n-C₅H₁₁ 2-CH₃-3-Cl H O 867 neo-C₅H₁₁ 2-CH₃-3-Cl H O 868 c-C₅H₉ 2-CH₃-3-Cl H O 869 t-C₅H₁₁ 2-CH₃-3-Cl H O 870 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H S 213-214 871 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 200-202 872 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H S 873 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H S 874 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 875 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 876 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 877 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H S 878 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 879 neo-C₃H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 880 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H S 881 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H S 882 C₂H₅ 2-CH₃-3-Cl H S 883 n-C₃H₇ 2-CH₃-3-Cl H S 884 i-C₃H₇ 2-CH₃-3-Cl H S 885 c-C₃H₅ 2-CH₃-3-Cl H S 886 n-C₄H₉ 2-CH₃-3-Cl H S 887 s-C₄H₉ 2-CH₃-3-Cl H S 888 i-C₄H₉ 2-CH₃-3-Cl H S 889 t-C₄H₉ 2-CH₃-3-Cl H S 890 n-C₅H₁₁ 2-CH₃-3-Cl H S 891 neo-C₅H₁₁ 2-CH₃-3-Cl H S 892 c-C₅H₉ 2-CH₃-3-Cl H S 206-208 893 t-C₅H₁₁ 2-CH₃-3-Cl H S 894 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 151-153 895 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 171-173 896 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 897 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 898 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 899 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 900 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 901 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 902 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 903 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 904 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 905 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NOCH₃ 906 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 907 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 151-153 908 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 909 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 910 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 911 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 912 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 913 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 914 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 915 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 916 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 917 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃

[0273] TABLE 7

mp No R³ X L M T ° C. 918 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 919 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 177- 180 920 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 921 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 922 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 923 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 924 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 925 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 926 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 927 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 928 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 929 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CH₂ 930 neo-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ 931 c-C₅H₉ 2-CH₃-3-Cl O CH₂ CH₂ 932 t-C₅H₁₁ 2-CH₃-3-Cl O CH₂ CH₂ 933 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 934 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 179- 181 935 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 936 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 937 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 938 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 939 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 940 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 941 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ O CH₂ 942 C₂H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 943 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 163- 165 944 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 945 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 946 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 947 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 948 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 949 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 950 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 951 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 952 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 953 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl O CH₂ CHOCH₃ 954 C₂H₅ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 955 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 167- 171 956 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 957 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 958 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 959 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 960 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 961 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 962 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 963 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 964 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 965 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl S CH₂ CH₂ 966 C₂H₅ 2-CH₃-3-Cl S CH₂ CH₂ 967 n-C₃H₇ 2-CH₃-3-Cl S CH₂ CH₂ 968 i-C₃H₇ 2-CH₃-3-Cl S CH₂ CH₂ 969 c-C₃H₅ 2-CH₃-3-Cl S CH₂ CH₂ 970 n-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ 971 s-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ 972 i-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ 973 t-C₄H₉ 2-CH₃-3-Cl S CH₂ CH₂ 974 n-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ 975 neo-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ 976 c-C₅H₉ 2-CH₃-3-Cl S CH₂ CH₂ 164- 167 978 t-C₅H₁₁ 2-CH₃-3-Cl S CH₂ CH₂ 979 C₂H₅ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 980 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 152- 155 981 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 982 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 983 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 984 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 985 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 986 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 987 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 988 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 989 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 990 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl NCH₃ CH₂ CH₂ 991 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 992 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 214- 217 993 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 994 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 995 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 996 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 997 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 998 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 999 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 1000 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 1001 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 1002 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ O 1003 C₂H₅ 2-CH₃-3-Cl CH₂ CH₂ O 1004 n-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ O 1005 i-C₃H₇ 2-CH₃-3-Cl CH₂ CH₂ O 1006 c-C₃H₅ 2-CH₃-3-Cl CH₂ CH₂ O 1007 n-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O 1008 s-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O 1009 i-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O 1010 t-C₄H₉ 2-CH₃-3-Cl CH₂ CH₂ O 1011 n-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O 1012 neo-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O 1013 c-C₅H₉ 2-CH₃-3-Cl CH₂ CH₂ O 1014 t-C₅H₁₁ 2-CH₃-3-Cl CH₂ CH₂ O 1015 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1016 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 211- 213 1017 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1018 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1019 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1020 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1021 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1022 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1023 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1024 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1025 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1026 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ S 1027 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1028 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 230- 233 1029 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1030 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1031 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1032 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1033 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1034 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1035 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1036 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1037 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1038 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO 1039 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1040 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 198- 200 1041 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1042 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1043 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1044 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1045 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1046 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1047 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1048 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1049 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1050 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ SO₂ 1051 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1052 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 157- 160 1053 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1054 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1055 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1056 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1057 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1058 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1059 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1060 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1061 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃ 1062 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₂ CH₂ NCH₃

[0274] TABLE 8

No R³ X R¹⁴ Z mp ° C. 1063 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1064 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ O 189-192 1065 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1066 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1067 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1068 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1069 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1070 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1071 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1072 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1073 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1074 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1075 C₂H₅ 2-CH₃-3-Cl CH₃ O 1076 n-C₃H₇ 2-CH₃-3-Cl CH₃ O 1077 i-C₃H₇ 2-CH₃-3-Cl CH₃ O 1078 c-C₃H₅ 2-CH₃-3-Cl CH₃ O 1079 n-C₄H₉ 2-CH₃-3-Cl CH₃ O 1080 s-C₄H₉ 2-CH₃-3-Cl CH₃ O 1081 i-C₄H₉ 2-CH₃-3-Cl CH₃ O 1082 t-C₄H₉ 2-CH₃-3-Cl CH₃ O 1083 n-C₅H₁₁ 2-CH₃-3-Cl CH₃ O 1084 neo-C₅H₁₁ 2-CH₃-3-Cl CH₃ O 1085 c-C₅H₉ 2-CH₃-3-Cl CH₃ O 192-195 1086 t-C₅H₁₁ 2-CH₃-3-Cl CH₃ O 1087 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 239-241 1088 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 230-233 1089 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1090 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1091 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1092 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1093 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1094 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1095 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1096 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1097 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1098 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1099 C₂H₅ 2-CH₃-3-Cl H NCH₃ 1100 n-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1101 i-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1102 c-C₃H₅ 2-CH₃-3-Cl H NCH₃ 1103 n-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1104 s-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1105 i-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1106 t-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1107 n-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1108 neo-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1109 c-C₅H₉ 2-CH₃-3-Cl H NCH₃ 1110 t-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1111 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1112 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 211-215 1113 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1114 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1115 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1116 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1117 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1118 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1119 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1120 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1121 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1122 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0275] TABLE 9

No R³ X R¹⁴ Z mp ° C. 1123 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1124 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 217-220 1125 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1126 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1127 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1128 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1129 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1130 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1131 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1132 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1133 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1134 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1135 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1136 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 211-214 1137 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1138 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1139 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1140 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1141 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1142 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1143 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1144 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1145 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1146 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0276] TABLE 10

No R³ X R¹⁴ Z mp ° C. 1147 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1148 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 225-228 1149 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1150 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1151 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1152 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1153 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1154 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1155 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1156 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1157 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1158 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1159 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1160 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 220-224 1161 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1162 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1163 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1164 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1165 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1166 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1167 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1168 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1169 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1170 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0277] TABLE 11

No R³ X R¹⁴ Z mp ° C. 1171 CH₃ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 216-218 1172 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1173 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 213-216 1174 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1175 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1176 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1177 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1178 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1179 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1180 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1181 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1182 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1183 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1184 C₂H₅ 2-CH₃-3-Cl H NCH₃ 1185 n-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1186 i-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1187 c-C₃H₅ 2-CH₃-3-Cl H NCH₃ 1188 n-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1189 s-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1190 i-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1191 t-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1192 n-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1193 neo-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1194 c-C₅H₉ 2-CH₃-3-Cl H NCH₃ 1195 t-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1196 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1197 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 209-212 1198 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1199 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1200 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1201 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1202 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1203 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1204 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1205 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1206 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1207 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0278] TABLE 12

No R³ X R¹⁴ Z mp ° C. 1208 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1209 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 222-225 1210 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1211 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1212 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1213 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1214 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1215 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1216 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1217 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1218 n-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1219 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1220 C₂H₅ 2-CH₃-3-Cl H NCH₃ 1221 n-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1222 i-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1223 c-C₃H₅ 2-CH₃-3-Cl H NCH₃ 1224 n-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1225 s-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1226 i-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1227 t-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1228 n-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1229 neo-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1230 c-C₅H₉ 2-CH₃-3-Cl H NCH₃ 1231 t-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1232 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1233 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 215-218 1234 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1235 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1236 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1237 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1238 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1239 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1240 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1241 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1242 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1243 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0279] TABLE 13

No R³ X R¹⁴ Z mp ° C. 1244 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H O 1245 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 189-195 1246 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H O 1247 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H O 1248 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 1249 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 1250 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 1251 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H O 1252 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 1253 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 1254 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H O 1255 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H O 1256 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1257 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1258 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1259 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1260 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1261 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1262 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1263 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1264 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1265 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1266 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1267 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ O 1268 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1269 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 198-202 1270 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1271 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1272 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1273 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1274 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1275 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1276 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1277 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1278 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1279 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H NCH₃ 1280 C₂H₅ 2-CH₃-3-Cl H NCH₃ 1281 n-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1282 i-C₃H₇ 2-CH₃-3-Cl H NCH₃ 1283 c-C₃H₅ 2-CH₃-3-Cl H NCH₃ 1284 n-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1285 s-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1286 i-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1287 t-C₄H₉ 2-CH₃-3-Cl H NCH₃ 1288 n-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1289 neo-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1290 c-C₅H₉ 2-CH₃-3-Cl H NCH₃ 1291 s-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1292 t-C₅H₁₁ 2-CH₃-3-Cl H NCH₃ 1293 C₂H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1294 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 201-205 1295 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1296 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1297 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1298 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1299 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1300 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1301 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1302 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1303 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃ 1304 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl CH₃ NCH₃

[0280] TABLE 14

No R³ X (R⁹)_(n) mp ° C. 1305 C₂H₅ 2,6-(C₂H₅)₂-3-Cl H 218-220 1306 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H 184-186 1307 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl H 1308 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl H 1309 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H 1310 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H 1311 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H 148-150 1312 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl H 1313 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H 1314 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H 208-210 1315 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl H 174-176 1316 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl H 1317 C₂H₅ 2-CH₃-3-Cl H 1318 n-C₃H₇ 2-CH₃-3-Cl H 204-206 1319 i-C₃H₇ 2-CH₃-3-Cl H 1320 c-C₃H₅ 2-CH₃-3-Cl H 1321 n-C₄H₉ 2-CH₃-3-Cl H 1322 s-C₄H₉ 2-CH₃-3-Cl H 1323 i-C₄H₉ 2-CH₃-3-Cl H 1324 t-C₄H₉ 2-CH₃-3-Cl H 1325 n-C₅H₁₁ 2-CH₃-3-Cl H 1326 neo-C₅H₁₁ 2-CH₃-3-Cl H 1327 c-C₅H₉ 2-CH₃-3-Cl H 218-220 1328 t-C₅H₁₁ 2-CH₃-3-Cl H 1329 C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1330 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1331 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1332 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1333 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1334 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1335 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1336 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1337 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1338 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1339 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1340 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-CH₃ 1341 C₂H₅ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1342 n-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1343 i-C₃H₇ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1344 c-C₃H₅ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1345 n-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1346 s-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1347 i-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1348 t-C₄H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1349 n-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1350 neo-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1351 c-C₅H₉ 2,6-(C₂H₅)₂-3-Cl 6-Cl 1352 t-C₅H₁₁ 2,6-(C₂H₅)₂-3-Cl 6-Cl

[0281] Herbicides comprising, as an active ingredient thereof, the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof are useful for controlling annual and perennial weeds which grow in paddy fields, upland fields, orchards, swamps, etc., such as barnyard grass (Echinochloa crus-galli Beauv., an annual gramineous weed which is an injurious weed of paddy fields), umbrella plant (Cyperus difformis L., an annual cyperaceous grass which is an injurious weed of paddy fields), slender spikerush (Eleocharis acicularis Roem. et Schult, a perennial cyperaceous grass which is an injurious weed of paddy fields and which grows also in swamps and waterways), arrowhead (Saguittaria pygmaea Miq., an injurious perennial weed of Alismataceae family which grows in paddy fields, swamps and ditches), bulrush (Scirpus juncoides Roxb. var. horarui ohwi, a perennial cyperaceous weed which grows in paddy fields, swamps and ditches), foxtail grass (Alopecurus aegualis var. amurensis Ohwi, gramineous grass which grows in paddy fields and low swamps), wild oats (Avena fatua L., a biennial gramineous grass which grows in plains, waste lands and upland fields), mugwort (Artemisia princeps Pamp., a perennial composite grass which grows in cultivated and uncultivated fields and mountains), large crabgrass (Digitaria adscenducus Henr., an annual gramineous grass which is a strongly injurious weed of upland fields and orchards), Gishigishi or Japanese dock (Rumex japonicus Houtt., a perennial polygonaceous weed which grows in upland fields and roadsides), umbrella sedge (Cyperus iria L., an annual cyperaceous weed), redroot pigweed (Amaranthus varidis L., an annual weed of Amaranthaceae family which grows in vacant lands, roadsides and upland fields), cocklebur (Xanthium strumarium L., an injurious annual composite weed which grows in upland fields), velvetleaf (Abutilon theophrasti L., an injurious annual weed of Malvaceae family which grows in upland fields), purple thornapple (Dutura tatula L., an annual injurious weed of Convolvulaceae family which grows in upland fields), bird's eye speedwell (Veronica persica Poir., an injurious biennual weed of Scrophulariaceae family which grows in upland fields) and cleavers (Galium aparine L., an injurious annual weed of Rubiaceae family which grows in upland fields and orchards), and especially useful for controlling weeds such as barnyard grass and bulrush in paddy fields.

[0282] Since the herbicides comprising, as an active ingredient thereof, the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof exhibit an excellent controlling effect on weeds before or after emergence, the characteristic physiological activities of the herbicides can be effectively manifested by treating fields with the herbicides before planting useful plants therein, or after planting useful plants therein (including the case in which useful plants are already planted as in orchards) but during the period from the initial stage of emergence of weeds to their growth stage.

[0283] However, the application of the herbicides of the present invention is not restricted only to the modes mentioned above. The herbicides of the present invention can be applied to control not only weeds which grow in paddy fields but also weeds which grow in other places such as fields after reaping, temporarily non-cultivated paddy fields and upland fields, ridges between fields, agricultural pathways, waterways, lands constructed for pasture, graveyards, parks, roads, playgrounds, unoccupied areas around buildings, developed lands, railways, forests and the like.

[0284] The treatment of target weeds with the herbicides is most effective in economy when the treatment is carried out not later than the initial stage of emergence of weeds. However, the time of application is not limited thereto, but it is also possible to control the weeds in the growth stage.

[0285] When the fused heterocyclic dicarboxylic acid diamide derivative of general formula (I) or a salt thereof is used a herbicide, the compound is usually formed into a preparation of convenient form according to the conventional method in the production of agricultural compositions.

[0286] The fused heterocyclic dicarboxylic acid diamide derivatives of general formula (I) or salt thereof according to the present invention are compounded together with adjuvants according to the need, then supported on an appropriate carrier by the procedure of dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion, and then formed into appropriate preparation form such as suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablet or the like, after which they are put to use.

[0287] The inert carrier used in the present invention may be any of a solid carrier and a liquid carrier. The materials which can constitute the solid carrier include, for example, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clay (e.g. kaolin, bentonite and acid clay), talc (e.g. talc and pyrophyllite), silica materials (e.g. diatomaceous earth, siliceous sand, mica, white carbon, i.e. synthetic high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of the commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic or mineral powders, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like, and compost. These carriers may be used either alone or as a mixture of two or more carriers.

[0288] The liquid carrier is that which itself has a solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier, which can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichlorethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.

[0289] The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination of two or more adjuvants in some cases, or need not to be used at all.

[0290] To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene-sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

[0291] Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

[0292] To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

[0293] Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

[0294] Adjuvants such as silicone oil may also be used as a defoaming agent.

[0295] The content of the active ingredient may be varied according to the need. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrate and flowable wettable powder, too, the suitable content is from 0.01 to 50% by weight.

[0296] The herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof as an active ingredient is used to kill a variety of weeds or to suppress their growth in the following manner. That is, it is applied to weeds or foliage or soil in a place in which generation or growth of objective weed is undesirable either directly or after being properly diluted with or suspended in water or the like, in an amount effective for control of the weeds.

[0297] The applying dosage of the herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide derivative of general formula (I) or a salt thereof is varied depending upon various factors such as a purpose, weed to be controlled, a growth state of a plant, tendency of generation of weed, weather, environmental conditions, a preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of active ingredient compound) per hectare depending upon purpose.

[0298] The herbicide of the present invention comprising the fused heterocyclic dicarboxylic acid diamide of general formula (I) or a salt thereof as active ingredient may be used in admixture with other herbicides in order to expand both spectrum of controllable weeds and the period of time when effective applications are possible or to reduce the dosage.

EXAMPLES

[0299] Next, typical examples of the present invention and referential examples are presented below. The present invention is by no means limited by these examples.

Example 1

[0300] 1-1. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-7-fluoro-2-quinolinecarboxylic acid n-propylamide (Compound No. 158)

[0301] In 10 ml of tetrahydrofuran was dissolved 800 mg (2.41 mmol) of N-(3-chloro-2,6-diethylphenyl)-7-fluoro-2,3-quinolinedicarboximide. After adding 150 mg (2.5 mmol) of n-propylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0302] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 820 mg of the objective compound was obtained as a white crystalline product.

[0303] Property: m.p. 220-222° C.; Yield: 87%

[0304] 1-2. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-1,8-naphthylidine-2-carboxylic acid ethylamide (Compound No. 360)

[0305] In 10 ml of dioxane was dissolved 700 mg (1.91 mmol) of 2,3-carboximide. After adding 95 mg (2.3 mmol) of ethylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0306] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 620 mg of the objective compound was obtained as a white crystalline product.

[0307] Property: m.p. 249-264° C.; Yield: 80%

[0308] 1-3. Production of 3-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2-carboxylic acid n-propylamide (Compound No. 462)

[0309] In 10 ml of dioxane was dissolved 770 mg (2.08 mmol) of N-(3-chloro-2,6-diethylphenyl)-7,8-dihydro-5H-pyrano[4,3-b]pyridine-2,3-carboximide. After adding 127 mg (2.3 mmol) of n-propylamine to the solution obtained above, a reaction was carried out for 12 hours.

[0310] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 735 mg of the objective compound was obtained as a white crystalline product.

[0311] Property: m.p. 166-170° C.; Yield: 83%

Example 2

[0312] 2-1. Production of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydro-1-oxo-thieno[2,3-b]pyridine-5-carboxylic acid n-propylamide (Compound No. 1028)

[0313] In 10 ml of chloroform was dissolved 500 mg (1.16 mmol) of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-2,3-dihydrothieno[2,3-b]pyridine-5-carboxylic acid n-propylamide. After adding 200 mg (1.1 mmol) of m-chloroperbenzoic acid to the solution obtained above at 0° C., a reaction was carried out at ambient temperature for 6 hours.

[0314] After completion of the reaction, the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent, whereby 400 mg of the objective compound was obtained as a white crystalline product.

[0315] Property: m.p. 230-233° C.; Yield: 77%

[0316] 2-2. Production of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydro-1,1-dioxo-thieno[2,3-b]pyridine-5-carboxylic acid n-propylamide (Compound No. 1040)

[0317] In 10 ml of chloroform was dissolved 500 mg (1.16 mmol) of 6-(3-chloro-2,6-diethylphenyl)-aminocarbonyl-2,3-dihydrothieno[2,3-b]pyridine-5-carboxylic acid n-propylamide. After adding 400 mg (2.2 mmol) of m-chloroperbenzoic acid to the solution obtained above at 0° C., a reaction was carried out at ambient temperature for 6 hours.

[0318] After completion of the reaction, the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent, whereby 450 mg of the objective compound was obtained as a white crystalline product.

[0319] Property: m.p. 198-200° C.; Yield: 84%

Referential Example 1 Production of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5-carboxylic Acid

[0320] In 100 ml of tetrahydrofuran was dissolved 8.0 g (39.4 mmol) of 1-methyl-pyrazolo[5,4-b]pyridine-5,6-dicarboxylic acid anhydride. After adding 7.23 g (39.4 mmol) of 3-chloro-2,6-diethylaniline to the solution obtained above, a reaction was carried out at ambient temperature for 12 hours.

[0321] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the deposited crystal was washed with a small quantity of ether. Thus, 12.0 g (yield 79%) of the objective compound was obtained.

[0322]^(—)H-NMR[TMS/CDCl₃, δ (ppm)]

[0323] 1.21(3H,t,J=7.5 Hz), 1.26(3H,t,J=7.5 Hz),

[0324] 2.63(2H,q,J=7.5 Hz), 2.83(2H,q,J=7.5 Hz),

[0325] 4.27(3H,s), 7.18(1H,d,J=8.4 Hz),

[0326] 7.41(1H,d,J=8.4 Hz), 8.30(1H,s), 9.43(1H,s),

[0327] 10.10 (1H,bs)

Referential Example 2 Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5,6-carboximide

[0328] In 30 ml of trifluoroacetic acid was dissolved 9.0 g (23.3 mmol) of 6-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[5,4-b]pyridine-5-carboxylic acid. After adding 4.90 g (23.3 mmol) of trifluoroacetic acid anhydride to the solution obtained above, a reaction was carried out under reflux for 4 hours.

[0329] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 8.0 g (yield 93%) of the objective compound was obtained.

[0330]¹H-NMR(TMS/CDCl₃, δ (ppm)]

[0331] 1.09(3H,t,J=7.5 Hz), 1.13(3H,t,J=7.5 Hz),

[0332] 2.43(2H,q,J=7.5 Hz), 2.62(2H,q,J=7.5 Hz),

[0333] 4.34(3H,s), 7.20(1H,d,J=8.4 Hz),

[0334] 7.47(1H,d,J=8.4 Hz), 8.35(1H,s), 8.67(1H,s)

Referential Example 3 Production of N-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[4,5-b]pyridine-5,6-carboximide

[0335] In 30 ml of trifluoroacetic acid was dissolved 7.5 g (19.4 mmol) of 5-(3-chloro-2,6-diethylphenyl)aminocarbonyl-1-methyl-pyrazolo[4,5-b]pyridine-6-carboxylic acid. After adding 4.08 g (19.4 mmol) of trifluoroacetic acid anhydride to the solution obtained above, a reaction was carried out under reflux for 4 hours.

[0336] After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography using ethyl acetate/n-hexane as an eluent. Thus, 6.5 g (yield 91%) of the objective compound was obtained.

[0337]¹H-NMR[TMS/CDCl₃δ (ppm)]

[0338] 1.08(3H,t,J=7.5 Hz), 1.12(3H,t,J=7.5 Hz),

[0339] 2.43(2H,q,J=7.5 Hz), 2.63(2H,q,J=7.5 Hz),

[0340] 4.27(3H,s), 7.20(1H,d,J=8.4 Hz),

[0341] 7.48(1H,d,J=8.4 Hz), 8.37(1H,s), 8.53(1H,s)

[0342] Next, typical preparation examples and test examples of the present invention are shown below. The present invention is by no means limited to these examples.

[0343] In the preparation examples, the term “part” means part by weight.

Preparation Example 1

[0344] Each compound listed in Tables 1 to 14 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate

[0345] An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

Preparation Example 2

[0346] Each compound listed in Tables 1 to 14  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

[0347] A dust was prepared by mixing uniformly and grinding the above ingredients.

Preparation Example 3

[0348] Each compound listed in Tables 1 to 14  5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate  5 parts

[0349] Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

Preparation Example 4

[0350] Each compound listed in Tables 1 to 14 20 parts Mixture of kaolin and synthetic high-dispersion silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate  5 parts

[0351] A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1 Test for Herbicidal Effect on Paddy Field Weeds Before Emergence

[0352] Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass (Echinochloa crus-galli Beauv.) and bulrush (Scirpus juncoides Roxb.) were made to be before germination. The soil in the pots were treated with a solution containing a predetermined dosage of a chemical agent comprising a compound of the present invention listed in Tables 1 to 14.

[0353] Twenty one days after the treatment, the herbicidal effect was investigated, the result was compared with that in untreated plot to calculate the weed-controlling rate, and the herbicidal effect was judged according to the following criterion:

[0354] 5—Weed-killing rate is 100%.

[0355] 4—Weed-killing rate is 90-99%.

[0356] 3—Weed-killing rate is 70-89%.

[0357] 2—Weed-killing rate is 40-69%.

[0358] 1—Weed-killing rate is 1-39%.

[0359] 0—Weed-killing rate is 0%.

[0360] The results are shown in Table 15.

Test Example 2 Test for Herbicidal Effect on Paddy Field Weeds after Emergence

[0361] Soil was filled into {fraction (1/10000)} are pots and brought into a state of paddy field, in which seeds of barnyard grass (Echinochloa crus-galli Beauv.), bulrush (Scirpus juncoides Roxb.) and monochoria (Monochoria vaginalis Presl) were made to reach one-leaved stage. The soil in the pots were treated with a solution containing a predetermined dosage of a chemical agent comprising a compound of the present invention listed in Tables 1 to 14.

[0362] Twenty one days after the treatment, the herbicidal effect was investigated and the result was compared with that in untreated plot to calculate the weed-controlling rate, and the herbicidal effect was judged according to the same criterion as in Test Example 1.

[0363] The results are shown in Table 15. TABLE 15 Pre-emergence treatment Post-emergence treatment Dosage Barnyard Barnyard Mono- No. (kg/ha) grass Bulrush grass Bulrush choria  1 5 5 5 4 4 5  2 5 5 5 4 4 5  3 5 5 5 4 4 5  28 5 3 3 3 3 4  29 5 4 3 3 3 4  30 5 5 4 3 3 5  43 5 4 2 3 2 4  44 5 4 3 3 2 4  53 5 5 2 3 2 4  58 5 4 3 3 3 4  71 5 5 5 3 3 5  97 5 3 1 2 1 3  99 5 5 5 5 5 5 100 5 5 5 5 5 5 101 5 5 5 5 5 5 126 5 3 2 2 1 3 127 5 4 3 4 4 5 128 5 5 5 5 5 5 129 5 5 5 5 5 5 130 5 5 5 5 5 5 157 5 5 5 5 5 5 158 5 5 5 5 5 5 189 5 5 4 4 3 5 200 5 4 2 3 1 3 201 5 3 2 3 1 3 219 5 5 5 4 4 5 224 5 5 3 3 2 3 228 5 5 4 3 2 4 234 5 5 2 3 2 4 243 5 3 1 3 1 3 246 5 4 1 2 1 3 275 5 5 5 5 4 5 276 5 5 5 3 4 5 289 5 5 5 5 4 5 290 5 5 5 5 5 5 291 5 5 4 5 4 5 305 5 5 4 4 3 5 310 5 4 3 3 2 5 334 5 5 4 4 4 5 339 5 4 3 3 2 4 343 5 5 3 3 3 5   359-1 5 5 5 5 5 5   359-2 5 5 5 5 5 5   359-3 5 5 5 5 5 5   359-4 5 5 5 5 5 5   359-5 5 5 5 5 5 5   359-6 5 5 5 5 5 5 360 5 5 5 5 5 5 361 5 5 5 5 5 5 375 5 5 5 5 5 5 388 5 5 5 5 5 5 414 5 5 5 5 5 5 423 5 5 5 5 5 5 431 5 5 5 5 5 5 438 5 5 5 5 5 5 447 5 5 5 5 5 5 450 5 5 5 5 5 5 462 5 5 5 5 5 5 474 5 5 5 5 5 5 486 5 5 5 5 5 5 498 5 5 5 5 5 5 510 5 5 5 5 5 5 519 5 5 5 5 5 5 527 5 5 5 5 5 5 534 5 5 5 5 5 5 558 5 5 5 5 5 5 570 5 5 5 5 5 5 582 5 5 5 5 5 5 606 5 5 5 5 5 5 630 5 5 5 5 5 5 654 5 5 3 3 1 4 678 5 5 5 5 5 5 679 5 5 5 5 5 5 703 5 5 5 5 5 5 724 5 5 5 5 5 5 727 5 5 5 5 5 5 739 5 5 5 5 5 5 760 5 5 5 5 5 5 763 5 4 3 4 3 5 774 5 5 5 5 5 5 775 5 5 5 5 5 5 796 5 5 5 5 5 5 798 5 5 5 5 5 5 799 5 5 5 5 5 5 811 5 5 5 5 5 5 814 5 5 5 5 5 5 824 5 5 5 5 5 5 836 5 5 5 5 5 5 847 5 5 5 5 5 5 870 5 5 5 5 5 5 871 5 5 5 5 5 5 892 5 5 5 5 5 5 894 5 5 5 5 5 5 895 5 5 5 5 5 5 907 5 5 5 5 5 5 919 5 5 5 5 5 5 934 5 5 5 5 5 5 943 5 5 5 5 5 5 955 5 5 5 5 5 5 976 5 5 5 5 5 5 980 5 5 5 5 5 5 992 5 5 5 5 5 5 1016  5 5 5 5 5 5 1028  5 5 5 5 5 5 1040  5 5 5 5 5 5 1052  5 5 5 5 5 5 1064  5 5 5 5 5 5 1085  5 5 5 5 5 5 1087  5 5 5 5 5 5 1088  5 5 5 5 5 5 1112  5 5 5 5 5 5 1124  5 5 5 5 5 5 1136  5 5 5 5 5 5 1148  5 5 5 5 5 5 1160  5 5 5 5 5 5 1171  5 5 5 5 5 5 1173  5 5 5 5 5 5 1197  5 5 5 5 5 5 1209  5 5 5 5 5 5 1233  5 5 5 5 5 5 1245  5 5 5 5 5 5 1269  5 5 5 5 5 5 1294  5 5 5 5 5 5 1305  5 5 5 5 5 5 1306  5 5 5 5 5 5 1311  5 5 5 5 5 5 1314  5 5 5 4 4 5 1315  5 5 5 5 5 5 1318  5 5 4 4 4 5 1327  5 5 4 4 4 5

Test Example 3 Herbicidal Effect on Upland Weeds Before Emergence

[0364] Polyethylene-made vats having a size of 10 cm (length)×20 cm (width)×5 cm (height) were filled with soil, sown with seeds of forxtail grass (Alopecurus aegualis var. amurensis Ohwi); abbreviated to Am), barnyard grass (Echinochloa crus-galli Beauv., abbreviated to Ec), velvetleaf (Abutilon theophtasti L., abbreviated to At), cocklebur (Xanthium strumarium L., abbreviated to Xs), cleavers (Galium aparine L., abbreviated to Ga) and bird's eye speedwell (Veronica persica Poir., abbreviated to Vp) and with seeds of wheat (abbreviated to Wh) and soybean plant (So) as upland crop plants, and then covered with soil. Then, a liquid preparation of an agent comprising a prescribed concentration of a compound of the present invention (the compounds listed in Tables 1-14) as active ingredient was sprayed.

[0365] Fourteen days after the treatment, the herbicidal effect was investigated, from which weed-killing rate was calculated in the same manner as in Test Example 1, and the herbicidal effect was judged.

[0366] At the same time, phytotoxicity to soybean plant and wheat was investigated and judged according to the criterion mentioned below.

[0367] Criterion for judgment of phytotoxicity:

[0368] 5—Crop-killing rate is 100%.

[0369] 4—Crop-killing rate is 90-99%.

[0370] 3—Crop-killing rate is 70-89%.

[0371] 2—Crop-killing rate is 40-69%.

[0372] 1—Crop-killing rate is 1-39%.

[0373] 0—Crop-killing rate is 0-20%

[0374] (No Phytotoxicity).

[0375] The results are summarized in Table 16. TABLE 16 Dosage Phytotoxicity Herbicidal effect No (kg/ha) Wh So Am Ec At Xs Ga Vp  1 5 3 1 4 5 5 5 4 5  2 5 3 1 5 5 5 5 5 5  3 5 2 1 5 5 5 5 5 5  28 5 1 0 4 3 4 3 3 4  29 5 4 1 4 4 5 4 4 5  30 5 3 1 5 5 5 4 4 5  43 5 1 0 4 3 4 3 3 4  44 5 1 0 4 3 4 2 4 4  53 5 1 0 4 4 4 2 3 4  58 5 2 1 4 4 5 4 4 5  71 5 4 0 4 4 5 3 4 5  97 5 1 0 3 2 3 1 1 3  99 5 1 2 4 5 5 5 5 5 100 5 1 3 4 5 5 5 4 5 101 5 2 2 4 5 5 4 4 5 126 5 1 0 3 3 3 2 2 3 127 5 1 1 3 4 3 2 2 4 128 5 2 1 4 4 4 3 4 5 129 5 3 1 5 5 5 5 5 5 130 5 0 0 4 5 5 4 5 5 157 5 3 1 4 5 5 4 4 5 158 5 4 1 4 5 5 4 5 5 189 5 2 0 3 4 4 3 3 4 200 5 0 0 3 3 3 2 2 3 201 5 0 0 3 2 3 2 2 3 219 5 2 1 4 5 5 3 4 5 224 5 1 0 3 4 4 3 3 4 228 5 0 0 3 3 4 2 2 4 234 5 0 0 3 3 3 2 2 3 243 5 0 0 2 3 3 2 2 3 246 5 1 0 3 4 4 3 3 4 275 5 1 0 3 4 4 3 3 4 276 5 2 0 4 5 5 4 4 5 289 5 2 1 4 5 5 3 4 5 290 5 2 1 5 5 5 4 5 5 291 5 1 0 4 5 5 4 5 5 305 5 2 0 4 5 4 3 3 4 310 5 2 0 4 4 4 3 3 4 334 5 2 0 4 4 5 3 3 4 339 5 1 0 4 4 4 2 3 4 343 5 0 0 3 4 3 2 3 4   359-1 5 0 0 5 5 5 5 5 5   359-2 5 0 1 5 5 5 5 5 5   359-3 5 0 0 5 5 5 5 5 5   359-4 5 0 2 5 5 5 5 5 5   359-5 5 0 0 5 5 5 5 5 5   359-6 5 0 0 5 5 5 5 5 5 360 5 4 3 5 5 5 5 5 5 361 5 4 4 5 5 5 5 5 5 375 5 3 3 5 5 5 5 5 5 388 5 5 4 5 5 5 5 5 5 414 5 5 4 5 5 5 5 5 5 423 5 5 4 5 5 5 5 5 5 431 5 3 3 4 5 5 4 4 5 438 5 5 5 5 5 5 5 5 5 447 5 5 4 5 5 5 5 5 5 450 5 4 4 5 5 5 4 4 5 462 5 5 5 5 5 5 5 5 5 474 5 4 3 5 5 5 4 4 5 486 5 4 4 5 5 5 5 5 5 498 5 4 4 5 5 5 4 4 5 510 5 5 4 5 5 5 5 5 5 519 5 5 4 5 5 5 5 5 5 527 5 5 5 5 5 5 4 5 5 534 5 4 3 5 5 5 5 5 5 558 5 5 5 5 5 5 5 5 5 570 5 4 4 5 5 5 5 5 5 582 5 4 4 5 5 5 5 5 5 606 5 4 3 5 5 5 4 4 5 630 5 4 3 5 5 5 4 4 5 654 5 3 1 4 4 5 3 3 4 678 5 4 2 4 5 5 3 3 5 679 5 4 2 4 5 5 4 4 5 703 5 4 2 4 5 5 4 4 5 724 5 4 3 4 4 4 3 4 5 727 5 4 4 5 5 5 4 4 5 739 5 5 4 5 5 5 5 5 5 760 5 4 3 5 5 5 4 5 5 763 5 4 3 4 5 5 4 4 5 774 5 5 4 5 5 5 5 5 5 775 5 5 5 5 5 5 5 5 5 796 5 5 4 5 5 5 4 5 5 798 5 5 4 5 5 5 5 5 5 799 5 5 5 5 5 5 5 5 5 811 5 5 4 5 5 5 5 5 5 814 5 4 3 5 5 5 4 4 5 824 5 5 5 5 5 5 5 5 5 836 5 5 4 5 5 5 5 5 5 847 5 5 4 5 5 5 5 5 5 870 5 4 3 5 5 5 5 5 5 871 5 5 4 5 5 5 5 5 5 892 5 4 3 5 5 5 4 5 5 894 5 5 4 5 5 5 5 5 5 895 5 5 4 5 5 5 5 5 5 907 5 5 4 5 5 5 5 5 5 919 5 5 5 5 5 5 5 5 5 934 5 5 4 5 5 5 4 5 5 943 5 4 3 5 5 5 5 5 5 955 5 5 3 5 5 5 5 5 5 976 5 5 4 5 5 5 5 5 5 980 5 5 4 5 5 5 5 5 5 992 5 5 5 5 5 5 5 5 5 1016  5 5 5 5 5 5 5 5 5 1028  5 5 4 5 5 5 5 5 5 1040  5 5 4 5 5 5 5 5 5 1052  5 5 3 5 5 5 5 5 5 1064  5 5 4 5 5 5 5 5 5 1085  5 5 4 5 5 5 5 5 5 1087  5 5 5 5 5 5 5 5 5 1088  5 5 5 5 5 5 5 5 5 1112  5 5 5 5 5 5 5 5 5 1124  5 5 5 5 5 5 5 5 5 1136  5 5 5 5 5 5 5 5 5 1148  5 5 4 5 5 5 5 5 5 1160  5 5 4 5 5 5 5 5 5 1171  5 5 4 5 5 5 5 4 5 1173  5 5 5 5 5 5 5 5 5 1197  5 5 5 5 5 5 5 5 5 1209  5 5 5 5 5 5 5 5 5 1233  5 5 5 5 5 5 5 5 5 1245  5 5 5 5 5 5 5 5 5 1269  5 5 4 5 5 5 5 5 5 1294  5 5 4 5 5 5 5 5 5 1305  5 5 5 5 5 5 5 5 5 1306  5 5 5 5 5 5 5 5 5 1311  5 5 5 5 5 5 5 5 5 1314  5 4 3 5 5 5 4 4 5 1315  5 5 5 5 5 5 5 5 5 1318  5 5 3 5 5 5 4 4 5 1327  5 5 3 5 5 5 4 4 5

Test Example 4 Herbicidal Effect on Upland Weeds After Emergence

[0376] Polyethylene-made vats having a size of 10 cm (length)×20 cm (width)×5 cm (height) were filled with soil, sown with seeds of the following noxious upland weeds and with seeds of soybean plant and wheat as upland crop plants, and then covered with soil. The plants were made to grow up until they reached the leaf-stages mentioned below, after which an agent comprising a prescribed concentration of a compound of the present invention (listed in Tables 1 to 14) as active ingredient was sprayed.

[0377] Fourteen days after the treatment, the herbicidal effect was investigated, from which weed-killing rate was calculated in the same manner as in Test Example 1 and the results were judged. At the same time, phytotoxicity on soybean plant and wheat was investigated and judged in the same manner as in Test Example 3.

[0378] Sample weeds, their leaf stages, and leaf stages of soybean plant and wheat were as follows: Foxtail grass (Am) 1-2 leaved stage Barnyard grass (Ec) 1-2 leaved stage Velvetleaf (At) 2-leaved stage Cocklebur (Xs) 2-leaved stage Cleavers (Ga) 1-leaved stage Bird's eye speedwell (Vp) Cotyledon to 1-leaved stage Wheat (Eh) 2-leaved stage Soybean plant (So) 1-leaved stage

[0379] TABLE 17 Dosage Phytotoxicity Herbicidal effect No (kg/ha) Wh So Am Ec At Xs Ga Vp  1 5 2 1 3 4 5 4 3 5  2 5 2 1 4 5 5 4 5 5  3 5 3 2 5 5 5 4 5 5  28 5 1 0 2 3 3 2 2 4  29 5 1 0 3 3 4 3 3 4  30 5 2 1 4 4 5 3 3 5  43 5 1 0 2 3 3 2 1 3  44 5 1 0 3 3 3 2 3 4  53 5 1 0 3 3 4 2 2 3  58 5 3 2 4 4 5 3 3 4  71 5 4 2 4 4 4 3 3 5  97 5 0 0 2 2 2 1 1 3  99 5 4 2 4 5 5 4 4 5 100 5 2 3 4 5 5 4 5 5 101 5 3 2 4 5 5 4 4 5 126 5 0 0 2 2 3 1 1 3 127 5 2 1 3 3 3 1 2 3 128 5 2 1 4 4 4 3 3 5 129 5 4 2 5 5 5 5 5 5 130 5 3 1 4 5 5 4 4 5 157 5 3 2 4 5 5 4 4 5 158 5 4 2 4 5 5 4 5 5 189 5 2 0 3 3 4 2 3 4 200 5 0 0 2 3 3 1 1 3 201 5 0 0 3 2 3 1 1 3 219 5 2 1 4 5 5 3 3 5 224 5 2 1 3 4 4 2 2 4 228 5 1 1 3 3 4 1 2 4 234 5 0 0 2 3 3 1 1 3 243 5 0 0 2 3 3 1 1 3 246 5 1 0 3 3 4 2 2 4 275 5 2 1 3 4 4 3 3 4 276 5 3 2 4 5 5 4 4 5 289 5 2 1 4 5 5 3 4 5 290 5 3 2 5 5 5 4 5 5 291 5 2 2 4 5 5 4 4 5 305 5 2 1 3 4 4 2 2 4 310 5 2 0 3 4 4 3 2 3 334 5 2 1 3 4 4 3 3 4 339 5 2 1 3 4 4 2 2 4 343 5 0 0 2 4 3 2 2 3   359-1 5 2 3 5 5 5 5 5 5   359-2 5 3 4 5 5 5 5 5 5   359-3 5 2 3 5 5 5 5 5 5   359-4 5 2 4 5 5 5 5 5 5   359-5 5 3 2 5 5 5 5 5 5   359-6 5 2 3 5 5 5 5 5 5 360 5 4 3 5 5 5 5 4 5 361 5 5 4 5 5 5 5 5 5 375 5 4 4 5 5 5 5 5 5 388 5 5 4 5 5 5 5 5 5 414 5 5 4 5 5 5 5 5 5 423 5 5 4 5 5 5 5 5 5 431 5 4 3 4 4 5 4 4 5 438 5 5 4 5 5 5 5 5 5 447 5 5 4 5 5 5 5 5 5 450 5 4 4 5 5 5 4 4 5 462 5 5 5 5 5 5 5 5 5 474 5 3 3 5 5 5 4 4 5 486 5 4 4 5 5 5 5 5 5 498 5 4 4 5 5 5 4 4 5 510 5 5 4 5 5 5 5 5 5 519 5 5 4 5 5 5 5 5 5 527 5 5 5 5 5 5 4 5 5 534 5 4 4 5 5 5 5 5 5 558 5 5 5 5 5 5 5 5 5 570 5 4 4 5 5 5 4 4 5 582 5 4 4 5 5 5 5 5 5 606 5 4 3 5 5 5 4 4 5 630 5 4 3 5 5 5 4 4 5 654 5 3 2 3 3 4 2 2 4 678 5 4 3 4 5 5 3 3 5 679 5 3 2 4 5 5 4 4 5 703 5 3 2 4 5 5 4 4 5 724 5 3 2 4 4 4 3 4 5 727 5 4 4 5 5 5 4 4 5 739 5 5 4 5 5 5 5 5 5 760 5 4 3 5 5 5 4 5 5 763 5 4 3 4 5 5 4 4 5 774 5 5 4 5 5 5 5 5 5 775 5 5 5 5 5 5 5 5 5 796 5 4 4 5 5 5 4 4 5 798 5 5 4 5 5 5 5 5 5 799 5 5 5 5 5 5 5 5 5 811 5 5 4 5 5 5 4 4 5 814 5 4 3 5 5 5 4 4 5 824 5 5 4 5 5 5 5 5 5 836 5 5 4 5 5 5 5 5 5 847 5 5 4 5 5 5 5 5 5 870 5 4 3 5 5 5 5 5 5 871 5 5 4 5 5 5 5 5 5 892 5 4 3 5 5 5 4 4 5 894 5 5 4 5 5 5 4 5 5 895 5 5 4 5 5 5 5 5 5 907 5 5 4 5 5 5 5 5 5 919 5 5 5 5 5 5 5 5 5 934 5 5 4 5 5 5 4 5 5 943 5 4 4 5 5 5 5 5 5 955 5 5 3 5 5 5 5 5 5 976 5 5 4 5 5 5 5 5 5 980 5 5 4 5 5 5 5 5 5 992 5 5 5 5 5 5 5 5 5 1016  5 5 5 5 5 5 5 5 5 1028  5 5 4 5 5 5 5 4 5 1040  5 5 4 5 5 5 5 5 5 1052  5 5 3 5 5 5 5 5 5 1064  5 5 4 5 5 5 5 5 5 1085  5 5 4 5 5 5 5 4 5 1087  5 5 4 5 5 5 5 5 5 1088  5 5 5 5 5 5 5 5 5 1112  5 5 5 5 5 5 5 5 5 1124  5 5 5 5 5 5 5 5 5 1136  5 5 5 5 5 5 5 5 5 1148  5 5 4 5 5 5 5 5 5 1160  5 5 4 5 5 5 5 5 5 1171  5 4 3 5 5 5 4 4 5 1173  5 5 5 5 5 5 5 5 5 1197  5 5 5 5 5 5 5 5 5 1209  5 5 5 5 5 5 5 5 5 1233  5 5 5 5 5 5 5 5 5 1245  5 5 5 5 5 5 5 5 5 1269  5 5 4 5 5 5 5 5 5 1294  5 5 4 5 5 5 5 5 5 1305  5 5 5 5 5 5 5 5 5 1306  5 5 5 5 5 5 5 5 5 1311  5 5 5 5 5 5 5 5 5 1314  5 4 4 5 5 5 4 4 5 1315  5 5 5 5 5 5 5 5 5 1318  5 4 3 5 5 5 4 5 5 1327  5 4 3 5 5 5 4 5 5 

1. A fused heterocyclic dicarboxylic acid diamide derivative represented by general formula (I) or a salt thereof:

wherein R¹ represents hydrogen atom or (C₁-C₆) alkyl group; R² and R³ may be same or different and each represents hydrogen atom, (C₁-C₈) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₈) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C₁-C₆) alkoxy group, (C₁-C₁) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, alkylthio (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, amino (C₁-C₆) alkyl group, substituted amino (C₁-C₆) alkyl group substituted with one or two, same or different (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₆) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkoxy group or substituted phenyl (C₁-C₆) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups; or R² and R³, taken conjointly, represent a 5- to 6-membered heterocycle having at least one, same or different heteroatoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, further, the carbon atom or nitrogen atom on said heterocycle may have at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group and halo (C₁-C₆) alkylthio group; X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having, on the ring thereof, at least one, same or different halogen atoms, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, amino group, substituted amino group substituted with same or different (C₁-C₆) alkyl groups, cyano (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl groups, (C₁-C₆) acyl groups, (C₁-C₆) alkylsulfonyl groups or halo (C₁-C₆) alkylsulfonyl groups, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₁) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenyl (C₁-C₆) alkyl group or substituted phenyl (C₁-C₆) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group; and

represents Q¹, Q², Q³, Q⁴, Q⁵, Q⁶ Q⁷, Q⁸, Q⁹, Q¹⁰, Q¹¹, Q¹², Q1³ or Q¹⁴, wherein: Q¹ is a group of the following formula:

wherein Y represents hydrogen atom, halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, amino group, substituted amino group having at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₆) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group, (C₃-C₅) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C₁-C₆) alkyl groups; and R⁴ represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, nitro group, cyano group, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, methylenedioxy group, amino group and substituted amino group substituted with at least one, same or different (C₁-C₆) alkyl groups, cyano (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl groups, (C₁-C₆) alkoxycarbonyl groups, (C₁-C₆) alkoxyaminocarbonyl groups, (C₁-C₆) acyl groups, (C₁-C₆) alkylsulfonyl groups, halo (C₁-C₆) alkylsulfonyl groups or phenyl (C₁-C₆) alkyl groups; Q² is a group of the following formula:

wherein at least one of A, B, D and E represent a nitrogen atom, and the others of A, B, D and E represent C-R⁵ wherein R⁵ represents hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₁) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, amino group or substituted amino group having at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₆) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group; and Y is as defined above; Q³ is a group of the following formula:

wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R⁶ wherein R⁶ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group or halo (C₁-C₆) alkylsulfonyl group, and the others of F, G, J and K each represents C—(R⁷)R⁸ wherein R⁷ and R⁸ may be same or different and represent hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₆) alkyl group substituted with at least one, same or different halogen atoms or (C₁-C₆) alkyl groups, amino (C₁-C₆) alkyl group, substituted amino (C₁-C₆) alkyl group substituted with at least one, same or different (C₁-C₆) alkyl groups or phenyl (C₁-C₆) alkoxy group; and Y is as defined above; and G and J may be taken conjointly to represent CH═CH; Q⁴ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, nitro group, cyano group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₁) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkylsulfinyl group, halo (C₁-C₆) alkylsulfinyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkoxy group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group and phenyl group, amino group, substituted amino group substituted with at least one, same or different substituents selected from the group consisting of (C₁-C₆) alkyl group, cyano (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkoxyaminocarbonyl group, (C₁-C₆) acyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group and phenyl (C₁-C₆) alkyl group, (C₃-C₅) alkyleneimino group, hydrazino group or substituted hydrazino group substituted with same or different (C₁-C₆) alkyl groups; m represents an integer of 0 to 2; Z represents oxygen atom, sulfur atom or N-R¹⁰ wherein R¹⁰ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group or (C₁-C₆) alkylthio (C₁-C₆) alkyl group; and Y is as defined above; Q⁵ is a group of the following formula:

wherein R⁹, Y, Z and m are as defined above; Q⁶ is a group of the following formula:

wherein R⁹, Y, Z and m are as defined above; Q⁷ is a group of the following formula:

wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R¹¹ wherein R¹¹ represents hydrogen atom, hydroxyl group, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₁) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl group, (C₁-C₆) alkylsulfonyl group, halo (C₁-C₆) alkylsulfonyl group or (C₁-C₆) alkylthio (C₁-C₆) alkyl group, and the others of L, M and T each represents C—(R¹²)R¹³ wherein R¹² and R¹³ may be same or different and each represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₃-C₆) cycloalkyl (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group having at least one, same or different halogen atoms on the ring thereof, (C₁-C₆) alkoxy group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group, (C₁-C₆) alkoxycarbonyl (C₁-C₆) alkyl group, phenyl (C₁-C₆) alkyl group, substituted phenyl (C₁-C₁) alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, phenyl (C₁-C₆) alkoxy group, substituted phenyl (C₁-C₆) alkoxy group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atoms and (C₁-C₆) alkyl groups, amino (C₁-C₆) alkyl group or substituted amino (C₁-C₆) alkyl group substituted with at least one, same or different (C₁-C₆) alkyl groups; Q⁸ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom or is the same as R⁹, and Y and Z are as defined above; Q⁹ is a group of the following formula:

wherein R¹⁴, Y and Z are as defined above; Q¹⁰ is a group of the following formula:

wherein R¹⁴, Y and Z are as defined above; Q¹¹ is a group of the following formula:

wherein R Y and Z are as defined above; Q¹² is a group of the following formula:

wherein R¹⁴, Y and Z are as defined above; Q¹³ is a group of the following formula:

wherein R¹⁴, Y and Z are as defined above; and Q¹⁴ is a group of the following formula:

wherein R⁹ is as defined above and n represents an integer of 0 to
 4. 2. A fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to claim 1, wherein: R¹ represents hydrogen atom; R² and R³ may be same or different and each represents hydrogen atom, (C₁-C₈) alkyl group or (C₃-C₈) cycloalkyl group; and X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₃-C₆) cycloalkyl group, (C₁-C₆) alkoxy group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkylthio group, halo (C₁-C₆) alkylthio group, (C₁-C₆) alkoxy (C₁-C₆) alkyl group, (C₁-C₆) alkylthio (C₁-C₆) alkyl group and (C₁-C₆) alkoxycarbonyl group; and

represents Q¹, Q², Q³, Q⁴, Q⁵, Q⁶, Q⁷, Q⁸, Q⁹, Q10, Q¹¹, Q¹², Q¹³ or Q1⁴, wherein Q¹ is a group of the following formula:

wherein Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; R⁴ represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, hydroxyl group, (C₁-C₆) alkoxy group and methylenedioxy group; Q² is a group of the following formula:

wherein A represents nitrogen atom; B, D or E represents C—R⁵ wherein R⁵ represents hydrogen atom, halogen atom, (C₁-C₆) alkyl group or halo (C₁-C₁) alkyl group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₁) cycloalkyl group; Q³ is a group of the following formula:

wherein at least one of F, G, J and K represents oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N-R⁶ wherein R⁶ represents hydrogen atom, (C₁-C₆) alkyl group or halo (C₁-C₆) alkyl group, and the others of F, G, J and K represent C—(R⁷)R⁸ wherein R⁷ and R⁸ represent hydrogen atom; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and G and J may be taken conjointly to form CH═CH; Q⁴ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; m represents an integer of 0 to 2; Z represents oxygen atom, sulfur atom or N—R¹⁰ wherein R¹⁰ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Q⁵ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents oxygen atom or sulfur atom; Q⁶ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N—R¹⁰ wherein R¹⁰ is as defined above; Q⁷ is a group of the following formula:

wherein at least one of L, M and T represents oxygen atom, sulfur atom, sulfinyl group, sulfonyl group or N—R¹¹ wherein R¹¹ represents hydrogen atom, (C₁-C₆) alkyl group or halo (C₁-C₆) alkyl group; and the others of L, M and T represent C—(R¹²)R¹³ wherein R¹² and R¹³ may be same or different and represent hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₁-C₆) alkoxy group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Q⁸ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N-R¹⁰ wherein R¹⁰ is as defined above; Q⁹ is a group of the following formula:

wherein R ¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above; Q¹⁰ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above; Q¹¹ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above; Q¹² is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above; Q¹³ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above; and Q¹⁴ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and m represents an integer of 0 to
 2. 3. A fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to claim 2, wherein R¹ represents hydrogen atom; R² represents hydrogen atom; R³ represents hydrogen atom, (C₁-C₈) alkyl group or (C₃-C₈) cycloalkyl group; X represents 0 to 5, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group, (C₁-C₆) alkoxy group and halo (C₁-C₆) alkoxy group; and

represents Q¹, Q², Q³, Q⁴, Q⁵, Q⁷, Q⁸,or Q¹¹, wherein: Q¹ is a group of the following formula:

wherein Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and R⁴ represents 0 to 4, same or different substituents selected from the group consisting of halogen atom, (C₁-C₆) alkyl group, hydroxyl group, (C₁-C₆) alkoxy group and methylenedioxy group; Q² is a group of the following formula:

wherein A represents nitrogen atom; B, D or E represents C—R⁵ wherein R⁵ represents hydrogen atom, halogen atom, (C₁-C₆) alkyl group or halo (C₁-C₆) alkyl group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Q³ is a group of the following formula:

wherein at least one of F, G, J and K represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group or N—R⁶ wherein R⁶ represents hydrogen atom, (C₁-C₆) alkyl group or halo (C₁-C₆) alkyl group, and the others of F, G, J and K represent C—(R⁷)R⁸ wherein R⁷ and R⁸ represent hydrogen atom; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; further G and J may be taken conjointly to form CH═CH; Q⁴ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₁) cycloalkyl group; m represents an integer of 0 to 2; Z represents oxygen atom, sulfur atom or N—R¹⁰ wherein R¹⁰ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Q⁵ is a group of the following formula:

wherein R⁹ is same or different and represents halogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; m represents an integer of 0 to 2; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N-R¹⁰ wherein R¹⁰ is as defined above; Q⁷ is a group of the following formula:

wherein at least one of L, M and T represent oxygen atom, sulfur atom, sulfinyl group, sulfonyl group or N-R¹¹ wherein R¹¹ represents hydrogen atom, (C₁-C₆) alkyl group or halo (C₁-C₆) alkyl group, and the others of L, M and T represent C—(R¹²) R¹³ wherein R¹² and R¹³ may be same or different and each represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₁-C₆) alkoxy group; and Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Q⁸ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents oxygen atom, sulfur atom or N—R¹⁰ wherein R¹⁰ is as defined above; and Q¹¹ is a group of the following formula:

wherein R¹⁴ represents hydrogen atom, (C₁-C₆) alkyl group, halo (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; Y represents hydrogen atom, (C₁-C₆) alkyl group or (C₃-C₆) cycloalkyl group; and Z represents N-R¹⁰ wherein R¹⁰ is as defined above.
 4. A herbicide characterized by containing a fused heterocyclic dicarboxylic acid diamide derivative or a salt thereof according to any of claims 1 to 3 as an active ingredient.
 5. A method for using a herbicide characterized by applying an effective amount of a herbicide according to claim 4 to a weed or a soil for the purpose of controlling a weed undesirable for the growth of useful plants. 